(6-chloro-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-(3,4-dimethoxy-phenyl)-amine → N-(3,4-dimethoxyphenyl)-6-(1H-indazol-4-yl)-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine

HRID 876934Notes

Reaction equation

HRID 876934 reaction equation
Cl[C:2]1[N:7]=[C:6]2[N:8]([CH3:11])[N:9]=[CH:10][C:5]2=[C:4]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH3:22])[CH:14]=2)[N:3]=1.[NH:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:25](B2OC(C)(C)C(C)(C)O2)=[N:24]1>O>[CH3:22][O:21][C:15]1[CH:14]=[C:13]([NH:12][C:4]2[N:3]=[C:2]([C:27]3[CH:28]=[CH:29][CH:30]=[C:31]4[C:26]=3[CH:25]=[N:24][NH:23]4)[N:7]=[C:6]3[N:8]([CH3:11])[N:9]=[CH:10][C:5]=23)[CH:18]=[CH:17][C:16]=1[O:19][CH3:20]

Participants

4

Reactant 2

HCID 58345953(6-chloro-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-(3,4-dimethoxy-phenyl)-amineHCID 178431105HCID 178431105, compound

Product 1

HCID 44180021N-(3,4-dimethoxyphenyl)-6-(1H-indazol-4-yl)-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(6-Chloro-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-(3,4-dimethoxy-phenyl)-amine was reacted with indazole boronic acid pinacol ester in General Procedure A. Addition of water gave a solid which was purified by preparative HPLC to give 132. NMR: (CDCl3): 3.81 (s, 3H, CH3), 3.89 (s, H, ArH), 4.07 (s, 3H, CH3), 6.88 (d, H, ArH, J=8.52 Hz), 7.00 (dd, H, ArH, J=2.41 Hz, 8.46 Hz), 7.15-7.18 (m, 2H, 2×ArH), 7.43-7.47 (m, H, ArH), 7.54-7.56 (m, H, ArH), 8.33 (d, H, ArH, J=7.26 Hz), 9.08 (s, H, ArH), 10.1 (sbr, H, NH). MS: (ESI+) MH+=402.14

Workup

  1. customgave a solid which
  2. customwas purified by preparative HPLC

Sources & evidence

ORD record
ord-2e2177a2aec847bbb401454a238346a7
Source dataset
uspto-grants-2015_03
Patent number
US08987280B2

Reaction notes

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