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

HRID 531666Notes

Reaction equation

HRID 531666 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:40]=[CH:41][CH:42]=1)[CH2:5][N:6]1[CH:10]=[C:9]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[C:17]([C:20]4[CH:25]=[CH:24][C:23]([NH:26][CH:27]5[CH2:32][CH2:31][N:30](C(OC(C)(C)C)=O)[CH2:29][CH2:28]5)=[CH:22][CH:21]=4)[CH:18]=3)[NH:13][CH:12]=2)[CH:8]=[N:7]1>CO.CCOCC.Cl>[F:1][C:2]1[CH:3]=[C:4]([CH:40]=[CH:41][CH:42]=1)[CH2:5][N:6]1[CH:10]=[C:9]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[C:17]([C:20]4[CH:21]=[CH:22][C:23]([NH:26][CH:27]5[CH2:28][CH2:29][NH:30][CH2:31][CH2:32]5)=[CH:24][CH:25]=4)[CH:18]=3)[NH:13][CH:12]=2)[CH:8]=[N:7]1

Participants

3

Reactant 1

HCID 118523931tert-butyl 4-((4-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)amino)piperidine-1-carboxylate

Product 1

HCID 90031483N-(4-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl) piperidin-4-amineYield 75.4%

Reagents, catalysts & solvents 1

HCID 131735674methanol ether HClSolvent

Procedure

Using similar reaction conditions as described in step-ii of example-7, tert-butyl 4-((4-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)amino)piperidine-1-carboxylate (60 mg, 0.10 mmol) was deprotected in methanol/ether HCl (3.0/0.3 ml). This afforded 40 mg (75.4% yield) of the titled. 1H NMR (CD3OD, 400 MHz): δ 9.01-9.00 (d, 1H), 8.71-8.70 (d, 1H), 8.39 (s, 1H), 8.05 (s, 1H), 7.95 (s, 1H), 7.90-7.87 (m, 2H), 7.37-7.34 (m, 3H), 7.14-7.12 (s, 1H), 7.04-7.01 (m, 2H), 5.46 (s, 2H), 3.95-3.85 (m, 1H), 3.54-3.51 (d, 2H), 3.81-3.72 (t, 2H), 3.30-3.26 (d, 2H), 2.00-1.90 (m, 2H). MS: m/z=466.9 (M+1), HPLC: 96.60% in method A.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-3cff17fa92854fd6a2f03e6f018bf4f3
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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