tert-butyl 4-((3-(3-(1-phenethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)amino)piperidine-1-carboxylate → N-(3-(3-(1-phenethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperidin-4-amine

HRID 531655Notes

Reaction equation

HRID 531655 reaction equation
[CH2:1]([N:9]1[CH:13]=[C:12]([C:14]2[C:22]3[C:17](=[N:18][CH:19]=[C:20]([C:23]4[CH:24]=[C:25]([NH:29][CH:30]5[CH2:35][CH2:34][N:33](C(OC(C)(C)C)=O)[CH2:32][CH2:31]5)[CH:26]=[CH:27][CH:28]=4)[CH:21]=3)[NH:16][CH:15]=2)[CH:11]=[N:10]1)[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>Cl.CO>[CH2:1]([N:9]1[CH:13]=[C:12]([C:14]2[C:22]3[C:17](=[N:18][CH:19]=[C:20]([C:23]4[CH:24]=[C:25]([NH:29][CH:30]5[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]5)[CH:26]=[CH:27][CH:28]=4)[CH:21]=3)[NH:16][CH:15]=2)[CH:11]=[N:10]1)[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 1

HCID 118523994tert-butyl 4-((3-(3-(1-phenethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)amino)piperidine-1-carboxylate

Product 1

HCID 90031500N-(3-(3-(1-phenethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperidin-4-amineYield 27.4%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

Using similar reaction conditions as described in step-ii of example-7, tert-butyl 4-((3-(3-(1-phenethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)amino)piperidine-1-carboxylate (80 mg, 0.142 mmol) was deprotected in HCl in methanol (5 ml). This afforded 18 mg (21.9% yield) of the titled compound. 1H NMR (CD3OD, 400 MHz): δ 8.55 (s, 1H), 8.435-8.431 (d, 1H), 7.91 (s, 1H), 7.81 (s, 1H), 7.71 (s, 1H), 7.39-7.32 (t, 1H), 7.29-7.20 (t, 2H), 7.16-7.13 (m, 2H), 7.04-7.03 (m, 2H), 6.85-6.80 (d, 1H), 4.49-4.46 (t, 2H), 3.85-3.75 (m, 1H), 3.52-3.49 (m, 2H), 3.22-3.19 (m, 4H), 2.35-2.25 (dd, 2H), 1.80-1.65 (m, 2H). MS: m/z=463.3 (M+1), HPLC: 90.63% in method A.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-4dd0911c211b489ca4835705184d3876
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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