Ethanol → (2S)-1-(4-(4-(3-(1-(3-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperazin-1-yl)propan-2-ol

HRID 531732Notes

Reaction equation

HRID 531732 reaction equation
Cl.[F:2][C:3]1[CH:4]=[C:5]([CH:45]=[CH:46][CH:47]=1)[CH2:6][N:7]1[C:11]([CH3:12])=[C:10]([C:13]2[C:21]3[C:16](=[N:17][CH:18]=[C:19]([C:22]4[CH:27]=[CH:26][C:25]([N:28]5[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]5)=[CH:24][CH:23]=4)[CH:20]=3)[N:15]([S:34]([C:37]3[CH:43]=[CH:42][C:40]([CH3:41])=[CH:39][CH:38]=3)(=[O:36])=[O:35])[CH:14]=2)[C:9]([CH3:44])=[N:8]1.CCN(C(C)C)[CH:51]([CH3:53])[CH3:52].C([OH:59])C>>[F:2][C:3]1[CH:4]=[C:5]([CH:45]=[CH:46][CH:47]=1)[CH2:6][N:7]1[C:11]([CH3:12])=[C:10]([C:13]2[C:21]3[C:16](=[N:17][CH:18]=[C:19]([C:22]4[CH:27]=[CH:26][C:25]([N:28]5[CH2:29][CH2:30][N:31]([CH2:52][C@@H:51]([OH:59])[CH3:53])[CH2:32][CH2:33]5)=[CH:24][CH:23]=4)[CH:20]=3)[N:15]([S:34]([C:37]3[CH:43]=[CH:42][C:40]([CH3:41])=[CH:39][CH:38]=3)(=[O:35])=[O:36])[CH:14]=2)[C:9]([CH3:44])=[N:8]1

Participants

4

Reactant 3

HCID 702EthanolHCID 81531DiisopropylethylamineHCID 1185239813-(1-(3-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-5-(4-(piperazin-1-yl)phenyl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine hydrochloride

Product 1

HCID 90031229(2S)-1-(4-(4-(3-(1-(3-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperazin-1-yl)propan-2-olYield 82%

Procedure

Using similar reaction conditions as described in step-i of example-82A, 3-(1-(3-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-5-(4-(piperazin-1-yl)phenyl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine hydrochloride (197 mg, 0.294 mmol), DIPEA (76 mg, 0.588 mmol) and ethanol (4 mL) to get 167 mg (82.0%) of the titled compound. MS: m/z=693.7 (M+1).

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-d4915d7660e34a6c87aa2e90e510c965
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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