Dimethylamine → 1-(dimethylamino)-3-(5-methoxy-3-(1-methyl-6-tosyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-7-yl)-1H-indol-1-yl)propan-2-ol

HRID 1628009Notes

Reaction equation

HRID 1628009 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][CH:13]1[CH2:15][O:14]1)[CH:7]=[C:6]2[C:16]1[N:28]([S:29]([C:32]2[CH:38]=[CH:37][C:35]([CH3:36])=[CH:34][CH:33]=2)(=[O:31])=[O:30])[C:19]2=[N:20][CH:21]=[C:22]3[CH:26]=[N:25][N:24]([CH3:27])[C:23]3=[C:18]2[CH:17]=1.[CH3:39][NH:40][CH3:41]>CN(C=O)C>[CH3:39][N:40]([CH3:41])[CH2:15][CH:13]([OH:14])[CH2:12][N:8]1[C:9]2[C:5](=[CH:4][C:3]([O:2][CH3:1])=[CH:11][CH:10]=2)[C:6]([C:16]2[N:28]([S:29]([C:32]3[CH:38]=[CH:37][C:35]([CH3:36])=[CH:34][CH:33]=3)(=[O:31])=[O:30])[C:19]3=[N:20][CH:21]=[C:22]4[CH:26]=[N:25][N:24]([CH3:27])[C:23]4=[C:18]3[CH:17]=2)=[CH:7]1

Participants

4

Reactant 2

HCID 674Dimethylamine2×HCID 583819947-(5-methoxy-1-(oxiran-2-ylmethyl)-1H-indol-3-yl)-1-methyl-6-tosyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridine

Product 1

HCID 583820821-(dimethylamino)-3-(5-methoxy-3-(1-methyl-6-tosyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-7-yl)-1H-indol-1-yl)propan-2-olYield 99%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a flask, a mixture of 7-(5-methoxy-1-(oxiran-2-ylmethyl)-1H-indol-3-yl)-1-methyl-6-tosyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridine (0.212 mmol) in DMF (5 mL) and dimethylamine (0.054 mL, 1.061 mmol) was stirred for about 17 h at rt. Additional dimethylamine (0.054 mL, 1.061 mmol) was added and the mixture was heated to about 50° C. for about 5 h, then at rt for about 17 h. The mixture was concentrated in vacuo to provide 1-(dimethylamino)-3-(5-methoxy-3-(1-methyl-6-tosyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-7-yl)-1H-indol-1-yl)propan-2-ol (0.120 g, 99%): LC/MS (Table 2, Method c) Rt=1.29 min; MS m/z 573 (M+H)+.

Workup

  1. temperaturethe mixture was heated to about 50° C. for about 5 h
  2. waitat rt for about 17 h
  3. concentrationThe mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-ee4ccd631c40414b8456bc0b37875951
Source dataset
uspto-grants-2014_07
Patent number
US08785639B2

Reaction notes

Loading…