(2-Methyl-1,3-thiazol-5-yl)methanamine → 2-(3-(cyclopropylmethyl)-2-oxoimidazolidin-1-yl)-4-methyl-N-((2-methylthiazol-5-yl)methyl)thiazole-5-carboxamide

HRID 554994Notes

Reaction equation

HRID 554994 reaction equation
FC1C=C(CN)C=NC=1.[CH3:10][C:11]1[S:12][C:13]([CH2:16][NH2:17])=[CH:14][N:15]=1.[CH:18]1([CH2:21][N:22]2[CH2:26][CH2:25][N:24]([C:27]3[S:28][C:29]([C:33](O)=[O:34])=[C:30]([CH3:32])[N:31]=3)[C:23]2=[O:36])[CH2:20][CH2:19]1>>[CH:18]1([CH2:21][N:22]2[CH2:26][CH2:25][N:24]([C:27]3[S:28][C:29]([C:33]([NH:17][CH2:16][C:13]4[S:12][C:11]([CH3:10])=[N:15][CH:14]=4)=[O:34])=[C:30]([CH3:32])[N:31]=3)[C:23]2=[O:36])[CH2:19][CH2:20]1

Participants

4

Reactant 3

HCID 19046689(2-Methyl-1,3-thiazol-5-yl)methanamineHCID 45116207(5-Fluoropyridin-3-yl)methanamineHCID 579198202-(3-(Cyclopropylmethyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid

Product 1

HCID 579198552-(3-(cyclopropylmethyl)-2-oxoimidazolidin-1-yl)-4-methyl-N-((2-methylthiazol-5-yl)methyl)thiazole-5-carboxamideYield 65%

Procedure

Following the procedure as describe in Example 12, making variations as required to replace (5-fluoropyridin-3-yl)methanamine with (2-methylthiazol-5-yl)methanamine 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 65% yield: mp 165-167° C. (dichloromethane/hexanes); 1H NMR (300 MHz, CDCl3) δ 7.00 (s, 1H), 6.30-6.27 (m, 1H), 4.60 (d, J=5.4 Hz, 2H), 4.13-4.08 (m, 2H), 3.72-3.66 (m, 2H), 3.18 (d, J=7.1 Hz, 2H), 2.69 (s, 3H), 2.60 (s, 3H), 0.97-0.92 (m, 1H), 0.60-0.53 (m, 2H), 0.27-0.22 (m, 2H); 13C NMR (75 MHz, CDCl3) δ 166.6, 162.4, 157.6, 155.2, 152.9, 152.0, 117.2, 114.9, 48.6, 42.2, 42.1, 39.9, 19.1, 17.2, 8.9, 3.4; MS (ES+) m/z 392.0 (M+1).

Sources & evidence

ORD record
ord-94dd90902c1d454d8ab9af3aa0616781
Source dataset
uspto-grants-2011_11
Patent number
US08049016B2

Reaction notes

Loading…