Benzylamine → 1-(5-Acetyl-4-methylthiazol-2-yl)-3-(4-(piperidine-1-carbonyl)benzyl)imidazolidin-2-one

HRID 2067397Notes

Reaction equation

C(N)C1C=CC=CC=1.[NH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.[C:15]([C:18]1[S:22][C:21]([N:23]2[CH2:27][CH2:26][N:25]([CH2:28][C:29]3[CH:37]=[CH:36][C:32]([C:33](O)=[O:34])=[CH:31][CH:30]=3)[C:24]2=[O:38])=[N:20][C:19]=1[CH3:39])(=[O:17])[CH3:16]>>[C:15]([C:18]1[S:22][C:21]([N:23]2[CH2:27][CH2:26][N:25]([CH2:28][C:29]3[CH:37]=[CH:36][C:32]([C:33]([N:9]4[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]4)=[O:34])=[CH:31][CH:30]=3)[C:24]2=[O:38])=[N:20][C:19]=1[CH3:39])(=[O:17])[CH3:16]

Participants

Reactant 3

HCID 7504Benzylamine

HCID 8082Piperidine

HCID 580316644-((3-(5-Acetyl-4-methylthiazol-2-yl)-2-oxoimidazolidin-1-yl)methyl)benzoic acid

Product 1

HCID 580313851-(5-Acetyl-4-methylthiazol-2-yl)-3-(4-(piperidine-1-carbonyl)benzyl)imidazolidin-2-oneYield 54%

Procedure

Following the procedure as describe in Example 8, making variations as required to replace benzylamine with piperidine to react with 4-((3-(5-acetyl-4-methylthiazol-2-yl)-2-oxoimidazolidin-1-yl)methyl)benzoic acid, the title compound was obtained as a white powder in 54% yield: 1H NMR (300 MHz, CDCl3) δ 7.45-7.22 (m, 4H), 4.50 (s, 2H), 4.15-4.01 (m, 2H), 3.69-3.32 (m, 6H), 2.60 (s, 3H), 2.40 (s, 3H), 1.71-1.20 (m, 6H); MS (ES+) m/z 427.1 (M+1).

Sources & evidence

ORD record: ord-b7db4783e35b47f59c4e714dcb1aeb89
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08293768B2

Reaction notes

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