(6-Chloro-1,3-dimethyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-(3-methoxy-phenyl)-amine → 6-(1h-Indazol-4-yl)-n-(3-methoxyphenyl)-1,3-dimethyl-1h-pyrazolo[3,4-d]pyrimidin-4-amine

HRID 876935Notes

Reaction equation

HRID 876935 reaction equation
Cl[C:2]1[N:7]=[C:6]2[N:8]([CH3:12])[N:9]=[C:10]([CH3:11])[C:5]2=[C:4]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=2)[N:3]=1.[NH:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:24](B2OC(C)(C)C(C)(C)O2)=[N:23]1>>[NH:22]1[C:30]2[C:25](=[C:26]([C:2]3[N:7]=[C:6]4[N:8]([CH3:12])[N:9]=[C:10]([CH3:11])[C:5]4=[C:4]([NH:13][C:14]4[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=4)[N:3]=3)[CH:27]=[CH:28][CH:29]=2)[CH:24]=[N:23]1

Participants

3

Reactant 2

HCID 58345945(6-Chloro-1,3-dimethyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-(3-methoxy-phenyl)-amineHCID 178431105HCID 178431105, compound

Product 1

HCID 441802676-(1h-Indazol-4-yl)-n-(3-methoxyphenyl)-1,3-dimethyl-1h-pyrazolo[3,4-d]pyrimidin-4-amine

Procedure

(6-Chloro-1,3-dimethyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-(3-methoxyphenyl)-amine was reacted with indazole boronic acid pinacol ester using General Procedure A to give 141. NMR (CDCl3): 2.78 (3H, s), 3.89 (3H, s), 4.14 (3H, s), 6.79 (1H, dd), 7.02 (1H, br. s), 7.25 (1H, m), 7.37 (1H, t), 7.54 (1H, t), 7.63-7.68 (2H, m), 8.45 (1H, d), 9.10 (1H, s), 10.11 (1H, br). MS: MH+ 386.20 (100%)

Sources & evidence

ORD record
ord-69b0768e3f234283b82d77fe12705425
Source dataset
uspto-grants-2015_03
Patent number
US08987280B2

Reaction notes

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