886362-07-8 Usage
Uses
4-Methoxy-1H-indazol-3-amine is used as a reactant in the preparation and structure-activity relationship of indazole arylsulfonamides as allosteric CC-chemokine receptor 4 antagonists.
Synthesis
A mixture of 2-fluoro-6-(methyloxy)benzonitrile (8a) (10 g, 66 mmol) and hydrazine hydrate (9.63 mL, 198 mmol) in n-butanol (100 mL) was heated to reflux under nitrogen for 18 h. The reaction mixture was allowed to cool, water (300 mL) was added and the organic phase was removed. The solid in the aqueous phase was collected by filtration and dried in vacuo at 40 °C to give a white solid (0.6 g). The butanol phase was evaporated in vacuo and the residue and the aqueous mother liquors were combined and extracted using ethyl acetate (2 × 200 mL). The combined ethyl acetate extractions were dried (MgSO4) and evaporated in vacuo. The residue was dissolved in DCM and applied to a 100 g silica cartridge. This was eluted with cyclohexane (500 mL), cyclohexane ethyl acetate (1:1, 500 mL) and ethyl acetate (500 mL). The required fractions were combined and evaporated in vacuo to give 9a (9.92 g, 92%) as an off-white solid. MS ES + ve m/z 164 (M + H)+. 1H NMR δ (DMSO-d6) 11.35 (1H, s), 7.10 (1H, t, J = 8 Hz), 6.76 (1H, d, J = 8 Hz), 6.29 (1H, d, J = 8 Hz), 4.95 (2H, br s), 3.85 (3H, s).
Check Digit Verification of cas no
The CAS Registry Mumber 886362-07-8 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 8,8,6,3,6 and 2 respectively; the second part has 2 digits, 0 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 886362-07:
(8*8)+(7*8)+(6*6)+(5*3)+(4*6)+(3*2)+(2*0)+(1*7)=208
208 % 10 = 8
So 886362-07-8 is a valid CAS Registry Number.
InChI:InChI=1/C8H9N3O/c1-12-6-4-2-3-5-7(6)8(9)11-10-5/h2-4H,1H3,(H3,9,10,11)
886362-07-8Relevant articles and documents
COMPOUND, PREPARATION METHOD THEREFOR, AND USE THEREOF
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Paragraph 0047-0048, (2021/03/19)
The present disclosure provides a compound of formula I or a pharmaceutically acceptable salt, a solvate, or a prodrug thereof, wherein M is a monovalent alkali metal. The present disclosure also provides a method for preparing the compound or its pharmaceutically acceptable salt, solvate, or prodrug, and further provides a pharmaceutical composition containing the compound and its use in the preparation of a medicine, which can be used for the treatment of CCR4-mediated diseases.
INDAZOLE COMPOUNDS
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Page/Page column 31, (2012/03/26)
Indazole compounds, processes for their preparation, pharmaceutical compositions containing such compounds and their use in therapy.
Lead optimisation of the N1 substituent of a novel series of indazole arylsulfonamides as CCR4 antagonists and identification of a candidate for clinical investigation
Procopiou, Panayiotis A.,Ford, Alison J.,Graves, Rebecca H.,Hall, David A.,Hodgson, Simon T.,Lacroix, Yannick M.L.,Needham, Deborah,Slack, Robert J.
scheme or table, p. 2730 - 2733 (2012/05/31)
Synthesis and preliminary SAR of the N1 substituent of a novel series of indazole sulfonamide chemokine receptor 4 (CCR4) antagonist is reported. Compound 7r was identified for further development.
