3-Chloro-4-fluorobenzylamine → n-(3-Chloro-4-fluorobenzyl)-6-hydroxy-1-methyl-2,5-dioxo-1,2,3,5-tetrahydroimidazo[1,2-a]pyrimidine-7-carboxamide

HRID 458698Notes

Reaction equation

HRID 458698 reaction equation
[OH:1][C:2]1[C:7](=[O:8])[N:6]2[CH2:9][C:10](=[O:13])[N:11]([CH3:12])[C:5]2=[N:4][C:3]=1[C:14]([O:16]CC)=O.[Cl:19][C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][C:27]=1[F:28])[CH2:23][NH2:24]>>[Cl:19][C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][C:27]=1[F:28])[CH2:23][NH:24][C:14]([C:3]1[N:4]=[C:5]2[N:11]([CH3:12])[C:10](=[O:13])[CH2:9][N:6]2[C:7](=[O:8])[C:2]=1[OH:1])=[O:16]

Participants

3

Reactant 2

HCID 1445393-Chloro-4-fluorobenzylamineHCID 54725632Ethyl 6-hydroxy-1-methyl-2,5-dioxo-1,2,3,5-tetrahydroimidazo[1,2-a]pyrimidine-7-carboxylate

Product 1

HCID 54705623n-(3-Chloro-4-fluorobenzyl)-6-hydroxy-1-methyl-2,5-dioxo-1,2,3,5-tetrahydroimidazo[1,2-a]pyrimidine-7-carboxamideYield 52.6%

Procedure

Reaction of intermediate 13, ethyl 6-hydroxy-1-methyl-2,5-dioxo-1,2,3,5-tetrahydroimidazo[1,2-a]pyrimidine-7-carboxylate (0.050 g, 0.197 mmol) with 3-chloro-4-fluorobenzylamine (0.10 g, 0.63 mmol) as described in the preparation of example 1 gave 0.038 g (52% yield) of the title amide as a white solid. 1HNMR 400 MHz (DMSO-d6) δ (ppm): 3.15 (3H, s, NCH3), 4.48 (2H, s, CH2), 4.49 (2H, d, J=6.4 Hz, NCH2), 7.3–7.55 (3H, m, aromatics), 9.50 (1H, broad t, NH), 12.16 (1H, s, OH). MS (ESI+) m/z 367 [M+H+].

Workup

  1. customas described in the preparation of example 1

Sources & evidence

ORD record
ord-85ed194a2d5042eba88578c2044ef934
Source dataset
uspto-grants-2007_03
Patent number
US07192948B2

Reaction notes

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