Trifluoroacetic acid → Trifluoroacetic acid

HRID 2092880Notes

Reaction equation

HRID 2092880 reaction equation
COC1C=C(OC)C=CC=1C[N:6]1[C:14]([CH3:16])([CH3:15])[C:13]2[C:12]([F:17])=[C:11]([NH:18][C@@H:19]3[CH2:24][CH2:23][CH2:22][CH2:21][C@@H:20]3[NH:25]C(=O)OC(C)(C)C)[N:10]=[C:9]([C:33]3[CH:34]=[N:35][N:36]([CH3:38])[CH:37]=3)[C:8]=2[C:7]1=[O:39].[C:46]([OH:52])([C:48]([F:51])([F:50])[F:49])=[O:47]>>[NH2:25][C@H:20]1[CH2:21][CH2:22][CH2:23][CH2:24][C@H:19]1[NH:18][C:11]1[N:10]=[C:9]([C:33]2[CH:34]=[N:35][N:36]([CH3:38])[CH:37]=2)[C:8]2[C:7](=[O:39])[NH:6][C:14]([CH3:16])([CH3:15])[C:13]=2[C:12]=1[F:17].[C:46]([OH:52])([C:48]([F:51])([F:50])[F:49])=[O:47]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86654745HCID 86654745, compound

Product 2

HCID 6422Trifluoroacetic acidYield 56%HCID 53251007HCID 53251007, compound

Procedure

A solution of tert-butyl (1S,2R)-2-(2-(2,4-dimethoxybenzyl)-7-fluoro-1,1-dimethyl-4-(1-methyl-1H-pyrazol-4-yl)-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)cyclo-hexylcarbamate (5 mg, 9.57 μmmol) in TFA (1 mL) was heated at 60° C. for 0.5 h. The reaction mixture was subsequently purified by preparative HPLC and the product lyophilized to give the title compound as a TFA salt (2 mg, 56%). [M+H] calc'd for C19H25FN6, 374. found, 374.

Workup

  1. customThe reaction mixture was subsequently purified by preparative HPLC

Sources & evidence

ORD record
ord-534561bd9ffa44b88df06bc124ab88c5
Source dataset
uspto-grants-2013_05
Patent number
US08440689B2

Reaction notes

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