tert-butyl (5-(3-(1-(3,5-difluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-3-methoxypyridin-2-yl)carbamate → 5-(3-(1-(3,5-difluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-3-methoxypyridin-2-amine

HRID 531869Notes

Reaction equation

HRID 531869 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:38]=[C:39]([F:41])[CH:40]=1)[CH2:5][N:6]1[C:10]([CH3:11])=[C:9]([C:12]2[C:20]3[C:15](=[N:16][CH:17]=[C:18]([C:21]4[CH:22]=[C:23]([O:35][CH3:36])[C:24]([NH:27]C(=O)OC(C)(C)C)=[N:25][CH:26]=4)[CH:19]=3)[NH:14][CH:13]=2)[C:8]([CH3:37])=[N:7]1>C(O)(C(F)(F)F)=O.C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([CH:38]=[C:39]([F:41])[CH:40]=1)[CH2:5][N:6]1[C:10]([CH3:11])=[C:9]([C:12]2[C:20]3[C:15](=[N:16][CH:17]=[C:18]([C:21]4[CH:22]=[C:23]([O:35][CH3:36])[C:24]([NH2:27])=[N:25][CH:26]=4)[CH:19]=3)[NH:14][CH:13]=2)[C:8]([CH3:37])=[N:7]1

Participants

3

Reactant 1

HCID 131735681tert-butyl (5-(3-(1-(3,5-difluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-3-methoxypyridin-2-yl)carbamate

Product 1

HCID 729432765-(3-(1-(3,5-difluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-3-methoxypyridin-2-amineYield 12.2%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

Using similar reaction conditions as described in step-ii of example-7, tert-butyl (5-(3-(1-(3,5-difluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-3-methoxypyridin-2-yl)carbamate (100 mg, 0.178 mmol) was deprotected in TFA/DCM (2/5 ml) to afford 10 mg (9.8% yield) of the titled compound. 1H NMR (CD3OD, 400 MHz): δ 8.56 (s, 1H), 8.14-8.13 (d, 1H), 7.70-7.69 (d, 2H), 7.53 (s, 1H), 6.91-6.86 (td, 1H), 6.79-6.76 (d, 2H), 5.36 (s, 2H), 4.07 (s, 3H), 2.20 (s, 3H), 2.18 (s, 3H). MS: m/z=461.3 (M+1), HPLC: 95.61% in method B.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-3f9a988141f34884b5d8434d31acfcb5
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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