Benzylamine → 1-(4-(5-methyl-1H-pyrazole-1-carbonyl)benzyl)-3-(4-methylthiazol-2-yl)imidazolidin-2-one

HRID 560627Notes

Reaction equation

HRID 560627 reaction equation
C(N)C1C=CC=CC=1.[CH3:9][C:10]1[CH:14]=[CH:13][NH:12][N:11]=1.[CH3:15][C:16]1[N:17]=[C:18]([N:21]2[CH2:25][CH2:24][N:23]([CH2:26][C:27]3[CH:35]=[CH:34][C:30]([C:31](O)=[O:32])=[CH:29][CH:28]=3)[C:22]2=[O:36])[S:19][CH:20]=1>>[CH3:9][C:10]1[N:11]([C:31]([C:30]2[CH:29]=[CH:28][C:27]([CH2:26][N:23]3[CH2:24][CH2:25][N:21]([C:18]4[S:19][CH:20]=[C:16]([CH3:15])[N:17]=4)[C:22]3=[O:36])=[CH:35][CH:34]=2)=[O:32])[N:12]=[CH:13][CH:14]=1

Participants

4

Reactant 3

HCID 7504BenzylamineHCID 580315034-((3-(4-Methylthiazol-2-yl)-2-oxoimidazolidin-1-yl)methyl)benzoic acidHCID 178428694HCID 178428694, compound

Product 1

HCID 580314691-(4-(5-methyl-1H-pyrazole-1-carbonyl)benzyl)-3-(4-methylthiazol-2-yl)imidazolidin-2-oneYield 24%

Procedure

Following the procedure as describe in Example 8, making variations as required to replace benzylamine with 3-methylpyrazole to react with 4-((3-(4-methylthiazol-2-yl)-2-oxoimidazolidin-1-yl)methyl)benzoic acid, the title compound was obtained as a white powder in 24% yield: mp 96-97° C. (ethyl acetate/hexanes); 1H NMR (300 MHz, CDCl3) δ 8.28 (d, J=2.7 Hz, 1H), 8.09 (d, J=8.4 Hz, 2H), 7.43 (d, J=8.4 Hz, 2H), 6.42 (d, J=0.9 Hz, 1H), 6.30 (d, J=2.7 Hz, 1H), 4.53 (s, 2H), 4.10-4.05 (m, 2H), 3.48-3.42 (m, 2H), 2.31 (s, 3H), 2.30 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 165.5, 158.7, 155.9, 154.6, 147.2, 141.1, 132.1, 131.3, 131.1, 127.7, 110.4, 106.9, 47.7, 42.3, 42.0, 17.3, 14.1; MS (ES+) m/z 382.2 (M+1).

Sources & evidence

ORD record
ord-6a0dce0fcf8c4d25845bcbf02c46dcc9
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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