2-(Aminomethyl)-5-fluoro-n-methylbenzamide trifluoroacetate salt → n-(4-Fluoro-2-(methylcarbamoyl)benzyl)-6-(benzyloxy)-1-isopropyl-5-oxo-1,2,3,5-tetrahydroimidazo[1,2-a]pyrimidine-7-carboxamide

HRID 1726891Notes

Reaction equation

HRID 1726891 reaction equation
[CH2:1]([O:8][C:9]1[C:14](=[O:15])[N:13]2[CH2:16][CH2:17][N:18]([CH:19]([CH3:21])[CH3:20])[C:12]2=[N:11][C:10]=1[C:22](O)=[O:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O.[NH2:32][CH2:33][C:34]1[CH:43]=[CH:42][C:41]([F:44])=[CH:40][C:35]=1[C:36]([NH:38][CH3:39])=[O:37]>>[F:44][C:41]1[CH:42]=[CH:43][C:34]([CH2:33][NH:32][C:22]([C:10]2[N:11]=[C:12]3[N:18]([CH:19]([CH3:20])[CH3:21])[CH2:17][CH2:16][N:13]3[C:14](=[O:15])[C:9]=2[O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:23])=[C:35]([C:36](=[O:37])[NH:38][CH3:39])[CH:40]=1

Participants

3

Reactant 2

HCID 210698142-(Aminomethyl)-5-fluoro-n-methylbenzamide trifluoroacetate saltHCID 575650136-(Benzyloxy) 1-isopropyl-5-oxo-1,2,3,5-tetrahydroimidazo[1,2-a]pyrimidine-7-carboxylic acid

Product 1

HCID 57565041n-(4-Fluoro-2-(methylcarbamoyl)benzyl)-6-(benzyloxy)-1-isopropyl-5-oxo-1,2,3,5-tetrahydroimidazo[1,2-a]pyrimidine-7-carboxamideYield 73%

Procedure

Coupling of 6-(benzyloxy)-1-isopropyl-5-oxo-1,2,3,5-tetrahydroimidazo[1,2-a]pyrimidine-7-carboxylic acid (0.300 g, 0.91 mmol) and 2-(aminomethyl)-5-fluoro-N-methylbenzamide trifluoroacetate salt (0.210 g, 0.96 mmol) as described for the synthesis of intermediate 3 gave 0.328 g (72% yield) of the title amide as white crystals; mp 197-198° C. (ethyl acetate). 1HNMR 400 MHz (CDCl3) δ (ppm): 1.23 (6H, d, J=6.8 Hz, 2×CH3), 2.98 (3H, d, J=5 Hz, NCH3), 3.66 (2H, t, J=9 Hz, CH2), 4.12 (2H, t, J=9 Hz, CH2), 4.43 (1H, m, CH), 4.48 (2H, d, J=6.3 Hz, NCH2), 5.09 (2H, s, OCH2), 7.05 (1H, m, aromatic), 7.13-7.17 (2H, m, aromatics), 7.3-7.35 (4H, m, NH and aromatics), 7.43-7.46 (2H, m, aromatics), 8.35 (1H, broad t, NH). Anal. Calcd for C26H28FN5O4: C, 63.27; H, 5.71; N, 14.19. Found: C, 63.06; H, 5.65; N, 14.02.

Sources & evidence

ORD record
ord-ce5eab1d57524e2984a1cd99a9944bb9
Source dataset
uspto-grants-2009_02
Patent number
US07494984B2

Reaction notes

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