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

HRID 531668Notes

Reaction equation

HRID 531668 reaction equation
C(OC([N:8]([CH:46]1[CH2:51][CH2:50][N:49](C(OC(C)(C)C)=O)[CH2:48][CH2:47]1)[C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[C:17]3[C:23]([C:24]4[C:25]([CH3:38])=[N:26][N:27]([CH2:30][C:31]5[CH:36]=[CH:35][CH:34]=[C:33]([F:37])[CH:32]=5)[C:28]=4[CH3:29])=[CH:22][N:21](C(OC(C)(C)C)=O)[C:18]3=[N:19][CH:20]=2)=[CH:11][CH:10]=1)=O)(C)(C)C>CO.CCOCC.Cl>[F:37][C:33]1[CH:32]=[C:31]([CH:36]=[CH:35][CH:34]=1)[CH2:30][N:27]1[C:28]([CH3:29])=[C:24]([C:23]2[C:17]3[C:18](=[N:19][CH:20]=[C:15]([C:12]4[CH:11]=[CH:10][C:9]([NH:8][CH:46]5[CH2:47][CH2:48][NH:49][CH2:50][CH2:51]5)=[CH:14][CH:13]=4)[CH:16]=3)[NH:21][CH:22]=2)[C:25]([CH3:38])=[N:26]1

Participants

3

Reactant 1

HCID 118523919tert-butyl 5-(4-((tert-butoxycarbonyl)(1-(tert-butoxycarbonyl)piperidin-4-yl)amino)phenyl)-3-(1-(3-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-1-carboxylate

Product 1

HCID 90030765N-(4-(3-(1-(3-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperidin-4-amineYield 31.2%

Reagents, catalysts & solvents 1

HCID 131735674methanol ether HClSolvent

Procedure

Using similar reaction conditions as described in step-ii of example-7, tert-butyl 5-(4-((tert-butoxycarbonyl)(1-(tert-butoxycarbonyl)piperidin-4-yl)amino)phenyl)-3-(1-(3-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-1-carboxylate (25 mg, 0.050 mmol) was deprotected in methanol/ether HCl (3/2 ml). This afforded 5 mg (31.2% yield) of the titled compound. 1H NMR (CD3OD, 400 MHz): δ 8.70 (s, 1H), 8.59 (s, 1H), 7.80 (s, 1H), 7.72-7.70 (d, 2H), 7.46-7.40 (m, 1H), 7.02-7.18 (d, 2H), 7.12-7.09 (m, 2H), 7.02-7.00 (d, 1H), 5.51 (s, 2H), 3.85-3.80 (m, 1H), 3.52-3.47 (d, 2H), 3.20-3.10 (t, 2H), 2.33-2.13 (m, 8H), 2.13-1.83 (m, 2H). MS: m/z=494.9 (M+1), HPLC: 95.22% in method B.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-d7ea3fe0417d4df98946511515d24388
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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