(6-chloro-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-(3-methanesulfonyl-benzyl)-amine → 6-(1h-Indazol-4-yl)-1-methyl-n-(3-(methylsulfonyl)benzyl)-1h-pyrazolo[3,4-d]pyrimidin-4-amine

HRID 876927Notes

Reaction equation

HRID 876927 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][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([S:20]([CH3:23])(=[O:22])=[O:21])[CH:15]=2)[N:3]=1.[NH:24]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:26](B2OC(C)(C)C(C)(C)O2)=[N:25]1>>[NH:24]1[C:32]2[C:27](=[C:28]([C:2]3[N:7]=[C:6]4[N:8]([CH3:11])[N:9]=[CH:10][C:5]4=[C:4]([NH:12][CH2:13][C:14]4[CH:19]=[CH:18][CH:17]=[C:16]([S:20]([CH3:23])(=[O:22])=[O:21])[CH:15]=4)[N:3]=3)[CH:29]=[CH:30][CH:31]=2)[CH:26]=[N:25]1

Participants

3

Reactant 2

HCID 58345948(6-chloro-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-(3-methanesulfonyl-benzyl)-amineHCID 178431105HCID 178431105, compound

Product 1

HCID 441800186-(1h-Indazol-4-yl)-1-methyl-n-(3-(methylsulfonyl)benzyl)-1h-pyrazolo[3,4-d]pyrimidin-4-amine

Procedure

(6-Chloro-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-(3-methanesulfonyl-benzyl)-amine was reacted with indazole boronic acid pinacol ester in General Procedure A. Purification on silica yielded 128. NMR (CDCl3) 3.03 (s, 3H, CH3), 4.20 (s, 3H, CH3), 5.13 (d, H, ArH, J=5.95 Hz), 5.84 (sbr, H, NH), 7.51-7.65 (m, 3H, 3×ArH), 7.79 (d, H, ArH, J=7.72 Hz), 7.91 (d, H, ArH, J=7.77 Hz), 7.93 (s, H, ArH), 8.09 (s, H, ArH), 8.39 (d, H, ArH, J=7.28 Hz), 9.04 (s, H, ArH), 10.13 (sbr, H, NH). MS: (ESI+) MH+=434.10

Workup

  1. customPurification on silica

Sources & evidence

ORD record
ord-7802ad252981406697e683118d5de122
Source dataset
uspto-grants-2015_03
Patent number
US08987280B2

Reaction notes

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