2-(Aminomethyl)-5-fluoro-n-methylbenzamide trifluoroacetate salt → HCID 57565066, compound

HRID 1726886Notes

Reaction equation

HRID 1726886 reaction equation
[CH2:1]([O:8][C:9]1[C:14](=[O:15])[N:13]2[CH2:16][CH2:17][N:18]([CH3:19])[C:12]2=[N:11][C:10]=1[C:20](O)=[O:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O.[NH2:30][CH2:31][C:32]1[CH:41]=[CH:40][C:39]([F:42])=[CH:38][C:33]=1[C:34]([NH:36][CH3:37])=[O:35]>>[F:42][C:39]1[CH:40]=[CH:41][C:32]([CH2:31][NH:30][C:20]([C:10]2[N:11]=[C:12]3[N:18]([CH3:19])[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:21])=[C:33]([C:34](=[O:35])[NH:36][CH3:37])[CH:38]=1

Participants

3

Reactant 2

HCID 210698142-(Aminomethyl)-5-fluoro-n-methylbenzamide trifluoroacetate saltHCID 57565016HCID 57565016, compound

Product 1

HCID 57565066HCID 57565066, compoundYield 54.4%

Procedure

Coupling of 6-(benzyloxy)-1-methyl-5-oxo-1,2,3,5-tetrahydroimidazo[1,2-a]pyrimidine-7-carboxylic acid (0.300 g, 1.0 mmol) and 2-(aminomethyl)-5-fluoro-N-methylbenzamide trifluoroacetate salt (0.295 g, 1.0 mmol) as described for the synthesis of intermediate 3 gave 0.253 g (54% yield) of the title amide as white crystals; mp 184° C. (ethyl acetate-hexane). 1HNMR 400 MHz (DMSO-d6) δ (ppm): 2.78 (3H, d, J=4.5 Hz, NCH3), 2.91 (3H, s, NCH3), 3.66 (2H, t, J=8.9 Hz, CH2), 4.02 (2H, t, J=8.9 Hz, CH2), 4.46 (2H, d, J=6.2 Hz, NCH2), 4.90 (2H, s, OCH2), 7.04 (1H, m, aromatic), 7.25 (1H, dd, J=2.6 Hz and J=9.1 Hz, aromatic), 7.29-7.46 (6H, m, aromatics), 8.49 (1H, broad q, NH), 8.78 (l H, broad t, NH). HRMS (ESI+) calculated for C24H25FN5O4 [M+H+]: 466.1891. found: 466.1899.

Sources & evidence

ORD record
ord-17010cf14882438c987f346beea82f6c
Source dataset
uspto-grants-2009_02
Patent number
US07494984B2

Reaction notes

Loading…