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

HRID 531644Notes

Reaction equation

HRID 531644 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]([CH:26]5[CH2:31][CH2:30][N:29](C(OC(C)(C)C)=O)[CH2:28][CH2:27]5)=[CH:22][CH:21]=4)[CH:18]=3)[NH:13][CH:12]=2)[C:8]([CH3:39])=[N:7]1>C(O)(C(F)(F)F)=O.CO>[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]([CH:26]5[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]5)=[CH:24][CH:25]=4)[CH:18]=3)[NH:13][CH:12]=2)[C:8]([CH3:39])=[N:7]1

Participants

3

Reactant 1

HCID 118524097tert-butyl 4-(4-(3-(1-(3-fluorobenzyl)-3-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperidine-1-carboxylate

Product 1

HCID 900310253-(1-(3-fluorobenzyl)-3-methyl-1H-pyrazol-4-yl)-5-(4-(piperidin-4-yl)phenyl)-1H-pyrrolo[2,3-b]pyridineYield 152%

Reagents, catalysts & solvents 1

HCID 86669916Methanol trifluoroacetic acidSolvent

Procedure

Using similar reaction conditions as described in step-ii of example-7, tert-butyl 4-(4-(3-(1-(3-fluorobenzyl)-3-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperidine-1-carboxylate (100 mg, 0.176 mmol) was deprotected in TFA/methanol (3/3 ml). This afforded 5 mg (152% yield) of the titled compound after purification by preparative HPLC along with one more isomer Example 91. 1H NMR (CD3OD, 300 MHz): δ 8.51 (s, 1H), 8.24 (s, 1H), 7.80 (s, 1H), 7.72-7.67 (m, 2H), 7.51 (s, 1H), 7.42-7.34 (m, 3H), 7.06-6.87 (m, 3H), 5.46 (s, 2H), 3.61-3.51 (m, 2H), 3.21-3.13 (m, 2H), 3.02-2.94 (t, 1H), 2.37 (s, 3H), 2.15-2.11 (m, 2H), 2.02-1.89 (m, 2H). MS: m/z=466.2 (M+1), HPLC: 89.39% in method B.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-c0860b8d407d45b1806e71ae5c21666e
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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