1-Propanol, 3-amino-2,2-dimethyl- → HCID 46220442, compound

HRID 241966Notes

Reaction equation

HRID 241966 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:16]=[CH:15][CH:14]=[C:13]3[C:9]=2[CH:10]=[N:11][NH:12]3)[N:5]=[C:4]2[N:17]([CH3:20])[N:18]=[CH:19][C:3]=12.[NH2:21][CH2:22][C:23]([CH3:27])([CH3:26])[CH2:24][OH:25]>>[NH:12]1[C:13]2[C:9](=[C:8]([C:6]3[N:5]=[C:4]4[N:17]([CH3:20])[N:18]=[CH:19][C:3]4=[C:2]([NH:21][CH2:22][C:23]([CH3:27])([CH3:26])[CH2:24][OH:25])[CH:7]=3)[CH:16]=[CH:15][CH:14]=2)[CH:10]=[N:11]1

Participants

3

Reactant 2

HCID 1173261-Propanol, 3-amino-2,2-dimethyl-HCID 580832344-Chloro-6-(1H-indazol-4-yl)-1-methyl-1H-pyrazolo[3,4-b]pyridine

Product 1

HCID 46220442HCID 46220442, compound

Procedure

4-Chloro-6-(1H-indazol-4-yl)-1-methyl-1H-pyrazolo[3,4-b]pyridine 7 (70 mg) and 3-amino-2,2-dimethyl-1-propanol (3 equiv.) were heated in microwave at 170° C. for two hours. Volatiles were removed in vacuo; the residue was purified by prep HPLC to give 114 as a white solid (55 mg). NMR (CDCl3): 1.11 (6H, s), 1.72 (1H, br, OH), 3.42 (2H, d), 3.64 (2H, d), 4.19 (3H, s), 5.70 (1H, br, NH), 6.78 (1H, s), 7.49-7.58 (2H, m), 7.71 (1H, d), 7.94 (1H, s), 8.82 (1H, s), 10.10 (1H, br, NH). MS: MH+ 351

Workup

  1. customVolatiles were removed in vacuo
  2. customthe residue was purified by prep HPLC

Sources & evidence

ORD record
ord-3153119023d6468b9965ccedd4eeeb24
Source dataset
uspto-grants-2014_02
Patent number
US08653098B2

Reaction notes

Loading…