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

HRID 531696Notes

Reaction equation

HRID 531696 reaction equation
Cl.[F:2][C:3]1[CH:4]=[C:5]([CH:45]=[CH:46][CH:47]=1)[CH2:6][N:7]1[CH:11]=[C:10]([C:12]2[C:20]3[C:15](=[N:16][CH:17]=[C:18]([C:21]4[CH:26]=[CH:25][C:24]([N:27]5[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]5)=[C:23]([O:33][CH3:34])[CH:22]=4)[CH:19]=3)[N:14]([S:35]([C:38]3[CH:44]=[CH:43][C:41]([CH3:42])=[CH:40][CH:39]=3)(=[O:37])=[O:36])[CH:13]=2)[CH:9]=[N:8]1.[CH3:48][C@H:49]1[CH2:51][O:50]1.CCN(C(C)C)C(C)C>C(O)C>[F:2][C:3]1[CH:4]=[C:5]([CH:45]=[CH:46][CH:47]=1)[CH2:6][N:7]1[CH:11]=[C:10]([C:12]2[C:20]3[C:15](=[N:16][CH:17]=[C:18]([C:21]4[CH:26]=[CH:25][C:24]([N:27]5[CH2:28][CH2:29][N:30]([CH2:48][C@@H:49]([OH:50])[CH3:51])[CH2:31][CH2:32]5)=[C:23]([O:33][CH3:34])[CH:22]=4)[CH:19]=3)[N:14]([S:35]([C:38]3[CH:39]=[CH:40][C:41]([CH3:42])=[CH:43][CH:44]=3)(=[O:36])=[O:37])[CH:13]=2)[CH:9]=[N:8]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 146262(2S)-2-MethyloxiraneHCID 900313783-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-5-(3-methoxy-4-(piperazin-1-yl)phenyl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine hydrochloride

Product 1

HCID 90030454(S)-1-(4-(4-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-methoxyphenyl)piperazin-1-yl)propan-2-olYield 68.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Using similar reaction conditions as described in step-i of example-82A, 3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-5-(3-methoxy-4-(piperazin-1-yl)phenyl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine hydrochloride (100 mg. 0.148 mmol) was alkylated using (S)-2-methyloxirane (26 mg, 0.445 mmol), DIPEA (115 mg, 0.891 mmol) and ethanol (5 mL) to get crude 70 mg of the titled compound. MS: m/z=695.3 (M+1).

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-d5a34a53c862413faa4c71b69aa6f042
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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