Oxazol-2-ylmethanamine → 2-(3-(cyclopropylmethyl)-2-oxoimidazolidin-1-yl)-4-methyl-N-(oxazol-2-ylmethyl)thiazole-5-carboxamide

HRID 554995Notes

Reaction equation

HRID 554995 reaction equation
FC1C=C(CN)C=NC=1.[O:10]1[CH:14]=[CH:13][N:12]=[C:11]1[CH2:15][NH2:16].[CH:17]1([CH2:20][N:21]2[CH2:25][CH2:24][N:23]([C:26]3[S:27][C:28]([C:32](O)=[O:33])=[C:29]([CH3:31])[N:30]=3)[C:22]2=[O:35])[CH2:19][CH2:18]1>>[CH:17]1([CH2:20][N:21]2[CH2:25][CH2:24][N:23]([C:26]3[S:27][C:28]([C:32]([NH:16][CH2:15][C:11]4[O:10][CH:14]=[CH:13][N:12]=4)=[O:33])=[C:29]([CH3:31])[N:30]=3)[C:22]2=[O:35])[CH2:18][CH2:19]1

Participants

4

Reactant 3

HCID 18947655Oxazol-2-ylmethanamineHCID 45116207(5-Fluoropyridin-3-yl)methanamineHCID 579198202-(3-(Cyclopropylmethyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid

Product 1

HCID 579197752-(3-(cyclopropylmethyl)-2-oxoimidazolidin-1-yl)-4-methyl-N-(oxazol-2-ylmethyl)thiazole-5-carboxamideYield 25%

Procedure

Following the procedure as describe in Example 12, making variations as required to replace (5-fluoropyridin-3-yl)methanamine with oxazol-2-ylmethanamine to react with 2-(3-(cyclopropylmethyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid, the title compound was obtained as a colorless solid in 25% yield: mp 172-174° C. (dichloromethane/hexanes); 1H NMR (300 MHz, CD3OD) δ 7.86 (s, 1H), 7.14-7.10 (m, 1H), 4.61 (s, 2H), 4.12-4.07 (m, 2H), 3.78-3.72 (m, 2H), 3.18 (d, J=7.1 Hz, 2H), 2.53 (s, 3H), 1.03-0.98 (m, 1H), 0.60-0.54 (m, 2H), 0.29-0.24 (m, 2H); MS (ES+) m/z 362.1 (M+1).

Sources & evidence

ORD record
ord-ca3bf84b5afb4ed78622e2464a640b84
Source dataset
uspto-grants-2011_11
Patent number
US08049016B2

Reaction notes

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