N-(6-chloro-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-N,N',N'-trimethyl-ethane-1,2-diamine → N1-(6-(1H-indazol-4-yl)-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-N1,N2,N2-trimethylethane-1,2-diamine

HRID 876932Notes

Reaction equation

HRID 876932 reaction equation
Cl[C:2]1[N:7]=[C:6]2[N:8]([CH3:11])[N:9]=[CH:10][C:5]2=[C:4]([N:12]([CH3:18])[CH2:13][CH2:14][N:15]([CH3:17])[CH3:16])[N:3]=1.[NH:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:21](B2OC(C)(C)C(C)(C)O2)=[N:20]1>>[NH:19]1[C:27]2[C:22](=[C:23]([C:2]3[N:7]=[C:6]4[N:8]([CH3:11])[N:9]=[CH:10][C:5]4=[C:4]([N:12]([CH3:18])[CH2:13][CH2:14][N:15]([CH3:17])[CH3:16])[N:3]=3)[CH:24]=[CH:25][CH:26]=2)[CH:21]=[N:20]1

Participants

3

Reactant 2

HCID 58345955N-(6-chloro-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-N,N',N'-trimethyl-ethane-1,2-diamineHCID 178431105HCID 178431105, compound

Product 1

HCID 44180022N1-(6-(1H-indazol-4-yl)-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-N1,N2,N2-trimethylethane-1,2-diamine

Procedure

N-(6-chloro-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-N,N′,N′-trimethyl-ethane-1,2-diamine was reacted with indazole boronic acid pinacol ester in General Procedure A. Purification on silica yielded 131. NMR: (CDCl3): 2.38 (s, 6H, 2×CH3), 2.73 (t, 2H, CH2, J=7.17 Hz), 3.54 (s, 311, CH3), 4.08 (m, 2H, CH2), 4.17 (s, 3H, CH3), 7.52 (t, H, ArH, J=7.77 Hz), 7.60 (d, H, ArH, J=8.27 Hz), 8.01 (s, H, ArH), 8.42 (d, H, ArH, J=7.23 Hz), 9.19 (s, H, ArH), 10.35 (sbr, H, NH). MS: (ESI+) MH+=351.18

Workup

  1. customPurification on silica

Sources & evidence

ORD record
ord-394236cbafb04800a598c654a4af2301
Source dataset
uspto-grants-2015_03
Patent number
US08987280B2

Reaction notes

Loading…