HCID 18442543, compound → HCID 54724255, compound

HRID 458700Notes

Reaction equation

HRID 458700 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[N:27]([CH3:28])[C:26](=[O:29])[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[N:27]([CH3:28])[C:26](=[O:29])[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 1

HCID 18442543HCID 18442543, compound

Product 1

HCID 54724255HCID 54724255, compoundYield 79.1%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of intermediate 15, N-{4-fluoro-2-(methylcarbamoyl)benzyl}-6-benzyloxy-1-methyl-2,5-dioxo-1,2,3,5-tetrahydroimidazo[1,2-a]pyrimidine-7-carboxamide, (0.179 g, 0.37 mmol) in trifluoroacetic acid (10 ml) was stirred at 22° C. for 2 h. The solvent was then evaporated in vacuo and the residue recrystallized from ethyl acetate to give 0.114 g (78% yield) of the title amide as a white solid. 1HNMR 400 MHz (DMSO-d6) δ (ppm): 2.79 (3H, d, J=4.3 Hz, NCH3), 3.12 (3H, s, NCH3), 4.48 (2H, s, CH2), 4.58 (2H, d, J=6.3 Hz, NCH2), 7.25–7.4 (3H, m, aromatics), 8.55 (1H, broad q, NH), 9.36 (1H, broad t, NH), 12.1 (1H, s, OH). MS (ESI+) m/z 390 [M+H+].

Workup

  1. customThe solvent was then evaporated in vacuo
  2. customthe residue recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-eb60120d45c04d1bac1b959afabbaac2
Source dataset
uspto-grants-2007_03
Patent number
US07192948B2

Reaction notes

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