Trifluoroacetic acid → N-(4-Fluoro-2-(methylcarbamoyl)benzyl)-3-hydroxy-8,8-dimethyl-4-oxo-4,6,7,8-tetrahydropyrrolo[1,2-a]pyrimidine-2-carboxamide

HRID 346481Notes

Reaction equation

HRID 346481 reaction equation
[F:1][C:2]1[CH:31]=[CH:30][C:5]([CH2:6][NH:7][C:8]([C:10]2[N:11]=[C:12]3[C:27]([CH3:29])([CH3:28])[CH2:26][CH2:25][N:13]3[C:14](=[O:24])[C:15]=2[O:16]CC2C=CC=CC=2)=[O:9])=[C:4]([C:32](=[O:35])[NH:33][CH3:34])[CH:3]=1.FC(F)(F)C(O)=O>>[F:1][C:2]1[CH:31]=[CH:30][C:5]([CH2:6][NH:7][C:8]([C:10]2[N:11]=[C:12]3[C:27]([CH3:29])([CH3:28])[CH2:26][CH2:25][N:13]3[C:14](=[O:24])[C:15]=2[OH:16])=[O:9])=[C:4]([C:32](=[O:35])[NH:33][CH3:34])[CH:3]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 21080176N-(4-Fluoro-2-(methylcarbamoyl)benzyl)-3-(benzyloxy)-8,8-dimethyl-4-oxo-4,6,7,8-tetrahydropyrrolo[1,2-a]pyrimidine-2-carboxamide

Product 1

HCID 54683249N-(4-Fluoro-2-(methylcarbamoyl)benzyl)-3-hydroxy-8,8-dimethyl-4-oxo-4,6,7,8-tetrahydropyrrolo[1,2-a]pyrimidine-2-carboxamide

Procedure

Intermediate 7, N-(4-fluoro-2-(methylcarbamoyl)benzyl)-3-(benzyloxy)-8,8-dimethyl-4-oxo-4,6,7,8-tetrahydropyrrolo[1,2-a]pyrimidine-2-carboxamide was treated with trifluoroacetic acid, according to Method D to provide the title compound 1H NMR (300 MHz, CDCl3) δ ppm: 12.12 (1H, br), 8.71 (1H, br), 7.47 (1H, dd, J=8.1, 5.5 Hz), 7.05–7.2 (2H, m), 6.26 (1H, br), 4.59 (2H, d, J=6.6 Hz), 3.95–4.06 (2H, m), 3.00 (3H, d, J=4.8 Hz), 1.99–2.08 (2H, m), 1.31 (6H, s); HRMS (ESI) calcd for C19H22FN4O4(M+H) 389.1625, found 389.1625.

Sources & evidence

ORD record
ord-be36a7e2994345fcaee6afca7861cb26
Source dataset
uspto-grants-2007_02
Patent number
US07173022B2

Reaction notes

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