Benzylamine → (R)-N-benzyl-2-(4-benzyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxamide

HRID 560656Notes

Reaction equation

HRID 560656 reaction equation
[CH2:1]([N:8]1CCN(C2SC(C(O)=O)=C(C)N=2)C1=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:23]([C@@H:30]1[CH2:34][N:33]([C:35]2[S:36][C:37]([C:41]([OH:43])=O)=[C:38]([CH3:40])[N:39]=2)[C:32](=[O:44])[NH:31]1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(N)C1C=CC=CC=1>>[CH2:1]([NH:8][C:41]([C:37]1[S:36][C:35]([N:33]2[CH2:34][C@@H:30]([CH2:23][C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[NH:31][C:32]2=[O:44])=[N:39][C:38]=1[CH3:40])=[O:43])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 7504BenzylamineHCID 579198662-(3-Benzyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acidHCID 66631090(R)-2-(4-benzyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid

Product 1

HCID 25094874(R)-N-benzyl-2-(4-benzyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxamideYield 10%

Procedure

Following the procedure as describe in Example 9, making variations as required to replace 2-(3-benzyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid with (R)-2-(4-benzyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid to react with benzylamine, the title compound was obtained as a white powder in 10% yield: mp 212-214° C.; 1H NMR (300 MHz, DMSO-d6) δ 8.43 (t, J=5.7 Hz, 1H), 8.02 (br s, 1H), 7.30-7.01 (m, 10H), 4.31 (d, J=5.7 Hz, 2H), 4.14-4.05 (m, 1H), 3.91 (t, J=10.2 Hz, 1H), 3.69-3.64 (m, 1H), 2.90-2.73 (m, 2H), 2.39 (s, 3H); 13C NMR (75 MHz, DMSO-d6) δ 162.1, 157.4, 156.2, 151.4, 140.1, 136.9, 129.8, 128.8, 128.6, 127.6, 127.1, 127.0, 118.0, 50.4, 48.9, 43.0, 41.1, 17.4; MS (ES+) m/z 407.0 (M+1).

Sources & evidence

ORD record
ord-0ec1f1174ea04724a6f7e8349f4d4c4a
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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