HCID 131735672, compound → HCID 90031226, compound

HRID 531616Notes

Reaction equation

HRID 531616 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:36]=[CH:37][CH:38]=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]=[C:22]([O:34][CH3:35])[C:23]([NH:26]C(=O)OC(C)(C)C)=[N:24][CH:25]=4)[CH:18]=3)[NH:13][CH:12]=2)[CH:8]=[N:7]1>C(O)(C(F)(F)F)=O.C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([CH:36]=[CH:37][CH:38]=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]=[C:22]([O:34][CH3:35])[C:23]([NH2:26])=[N:24][CH:25]=4)[CH:18]=3)[NH:13][CH:12]=2)[CH:8]=[N:7]1

Participants

3

Reactant 1

HCID 131735672HCID 131735672, compound

Product 1

HCID 90031226HCID 90031226, compoundYield 28%

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-fluorobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-3-methoxypyridin-2-yl)carbamate (120 mg, 0.233 mmol) was deprotected in TFA/DCM (1/5 ml). This afforded 27 mg (21.9% yield) of the titled compound. 1H NMR (DMSO-d6, 400 MHz): δ 8.577-8.572 (d, 1H), 8.417-8.413 (d, 1H), 8.37 (s, 1H), 8.03 (s, 2H), 7.956-7.953 (d, 1H), 7.86-7.79 (s, 1H), 7.799-7.793 (d, 1H), 7.40-7.39 (q, 1H), 7.12-7.07 (m, 3H), 5.40 (s, 2H), 4.06 (s, 3H). MS: m/z=415.6 (M+1), HPLC: 93.86% in method A.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-356a4c7679544bc399eaeba2b581643d
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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