tert-butyl 4-(4-(3-(3,5-dimethyl-1-(3-nitrobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperazine-1-carboxylate → tert-butyl 4-(4-(3-(1-(3-aminobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperazine-1-carboxylate

HRID 531556Notes

Reaction equation

HRID 531556 reaction equation
[CH3:1][C:2]1[C:6]([C:7]2[C:15]3[C:10](=[N:11][CH:12]=[C:13]([C:16]4[CH:21]=[CH:20][C:19]([N:22]5[CH2:27][CH2:26][N:25]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:24][CH2:23]5)=[CH:18][CH:17]=4)[CH:14]=3)[N:9]([S:35]([C:38]3[CH:44]=[CH:43][C:41]([CH3:42])=[CH:40][CH:39]=3)(=[O:37])=[O:36])[CH:8]=2)=[C:5]([CH3:45])[N:4]([CH2:46][C:47]2[CH:52]=[CH:51][CH:50]=[C:49]([N+:53]([O-])=O)[CH:48]=2)[N:3]=1>[Pd].C(O)C>[NH2:53][C:49]1[CH:48]=[C:47]([CH:52]=[CH:51][CH:50]=1)[CH2:46][N:4]1[C:5]([CH3:45])=[C:6]([C:7]2[C:15]3[C:10](=[N:11][CH:12]=[C:13]([C:16]4[CH:17]=[CH:18][C:19]([N:22]5[CH2:23][CH2:24][N:25]([C:28]([O:30][C:31]([CH3:34])([CH3:32])[CH3:33])=[O:29])[CH2:26][CH2:27]5)=[CH:20][CH:21]=4)[CH:14]=3)[N:9]([S:35]([C:38]3[CH:44]=[CH:43][C:41]([CH3:42])=[CH:40][CH:39]=3)(=[O:36])=[O:37])[CH:8]=2)[C:2]([CH3:1])=[N:3]1

Participants

4

Reactant 1

HCID 118524012tert-butyl 4-(4-(3-(3,5-dimethyl-1-(3-nitrobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperazine-1-carboxylate

Product 1

HCID 90031570tert-butyl 4-(4-(3-(1-(3-aminobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperazine-1-carboxylateYield 78.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Using similar reaction conditions as described in example-8, tert-butyl 4-(4-(3-(3,5-dimethyl-1-(3-nitrobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperazine-1-carboxylate (200 mg, 0.262 mmol) was reduced by 10% palladium on carbon (20 mg, 10% W/W), ethanol (3 mL) to yield 150 mg (yield 78.08%) of the titled compound. MS: m/z=7 32.3 (M+1).

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-573928a03dda49e59b72b8a6011336f2
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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