3-(Methylthio)propylamine → HCID 58083233, compound

HRID 241968Notes

Reaction equation

HRID 241968 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.[CH3:21][S:22][CH2:23][CH2:24][CH2:25][NH2:26]>>[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:26][CH2:25][CH2:24][CH2:23][S:22][CH3:21])[CH:7]=3)[CH:16]=[CH:15][CH:14]=2)[CH:10]=[N:11]1

Participants

3

Reactant 2

HCID 777433-(Methylthio)propylamineHCID 580832344-Chloro-6-(1H-indazol-4-yl)-1-methyl-1H-pyrazolo[3,4-b]pyridine

Product 1

HCID 58083233HCID 58083233, compound

Procedure

4-Chloro-6-(1H-indazol-4-yl)-1-methyl-1H-pyrazolo[3,4-b]pyridine 7 (100 mg) and 3-(methylthio)propylamine (3 equiv.) were heated in microwave at 170° C. for one hour following General Procedure B. Volatiles were removed in vacuo; the residue was purified by prep HPLC to give [6-(1H-indazol-4-yl)-1-methyl-1H-pyrazolo[3,4-b]pyridin-4-yl]-(3-methylsulfanyl-propyl)-amine (94 mg) as a white solid. 3-Chloroperoxybenzoic acid (MCPBA, 94 mg, 2.2 equiv.) in 2 ml dry DCM was added at 0° C. The reaction mixture was allowed slowly to warm up to room temperature over 3 hours and extracted with DCM, washed with saturated aqueous sodium hydrogen carbonate and purified by flash chromatography (methanol/DCM) to give 116 (27 mg) as a white solid. NMR (CDCl3): 2.39 (2H, m), 3.00 (3H, s), 3.25 (2H, t), 3.74 (2H, m), 4.20 (3H, s), 5.20 (1H, br t), 6.77 (1H, s), 7.50-7.54 (1H, m), 7.59 (1H, d), 7.70 (1H, d), 7.97 (1G=H, s), 8.82 (1H, s), 10.20 (1H, br). MS: MH+ 385.19 (100%)

Workup

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

Sources & evidence

ORD record
ord-d029b225cf5a4639a93f0663afc75834
Source dataset
uspto-grants-2014_02
Patent number
US08653098B2

Reaction notes

Loading…