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

HRID 531799Notes

Reaction equation

HRID 531799 reaction equation
Cl.[CH2:2]([O:9][C:10]1[CH:11]=[C:12]([CH:50]=[CH:51][CH:52]=1)[CH2:13][N:14]1[CH:18]=[C:17]([C:19]2[C:27]3[C:22](=[N:23][CH:24]=[C:25]([C:28]4[CH:29]=[N:30][C:31]([N:34]5[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]5)=[CH:32][CH:33]=4)[CH:26]=3)[N:21]([S:40]([C:43]3[CH:49]=[CH:48][C:46]([CH3:47])=[CH:45][CH:44]=3)(=[O:42])=[O:41])[CH:20]=2)[CH:16]=[N:15]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:53][C@H:54]1[CH2:56][O:55]1.CCN(C(C)C)C(C)C>C(O)C>[CH2:2]([O:9][C:10]1[CH:11]=[C:12]([CH:50]=[CH:51][CH:52]=1)[CH2:13][N:14]1[CH:18]=[C:17]([C:19]2[C:27]3[C:22](=[N:23][CH:24]=[C:25]([C:28]4[CH:33]=[CH:32][C:31]([N:34]5[CH2:35][CH2:36][N:37]([CH2:53][C@@H:54]([OH:55])[CH3:56])[CH2:38][CH2:39]5)=[N:30][CH:29]=4)[CH:26]=3)[N:21]([S:40]([C:43]3[CH:44]=[CH:45][C:46]([CH3:47])=[CH:48][CH:49]=3)(=[O:41])=[O:42])[CH:20]=2)[CH:16]=[N:15]1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 146262(2S)-2-MethyloxiraneHCID 1185240423-(1-(3-(benzyloxy)benzyl)-1H-pyrazol-4-yl)-5-(6-(piperazin-1-yl)pyridin-3-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine hydrochloride

Product 1

HCID 90030702(S)-1-(4-(5-(3-(1-(3-(benzyloxy)benzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)pyridin-2-yl)piperazin-1-yl)propan-2-ol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Using similar reaction conditions as described in step-i of example-82A, 3-(1-(3-(benzyloxy)benzyl)-1H-pyrazol-4-yl)-5-(6-(piperazin-1-yl)pyridin-3-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine hydrochloride (200 mg. 0.273 mmol) was alkylated using (S)-2-methyloxirane (48 mg, 0.819 mmol), DIPEA (211 mg, 1.638 mmol) and ethanol (20 mL) to get 200 mg (crude) of the titled compound. MS: m/z=754.3 (M+1).

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-08130a72aee1482490741ae19d90a7d1
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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