N-Benzyl-2-imino-4-methyl-2,3-dihydro-1,3-thiazole-5-carboximidic acid → HCID 59369670, compound

HRID 45381Notes

Reaction equation

HRID 45381 reaction equation
[O:1]=[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]1[C:8]1[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[CH:10][CH:9]=1.[CH2:17]([NH:24][C:25]([C:27]1[S:31][C:30]([NH2:32])=[N:29][C:28]=1[CH3:33])=[O:26])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>>[CH2:17]([NH:24][C:25]([C:27]1[S:31][C:30]([NH:32][C:12](=[O:14])[C:11]2[CH:10]=[CH:9][C:8]([N:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]3=[O:1])=[CH:16][CH:15]=2)=[N:29][C:28]=1[CH3:33])=[O:26])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

3

Reactant 2

HCID 210824N-Benzyl-2-imino-4-methyl-2,3-dihydro-1,3-thiazole-5-carboximidic acidHCID 184531904-(2-oxopyridin-1(2H)-yl)benzoic acid

Product 1

HCID 59369670HCID 59369670, compoundYield 58%

Procedure

Following the procedure as described in Example 11, making variations only as required to use 4-(2-oxopyridin-1-yl)-benzoic acid in place of 5-phenylpentanoic acid to react with 2-amino-4-methylthiazole-5-carboxylic acid benzylamide, the title compound was obtained as a white solid in 58% yield; 1H NMR (CDCl3, 300 MHz) δ 12.96 (s, 1H), 8.63 (t, J=5.9 Hz, 1H), 8.18 (d, J=8.6 Hz, 2H), 7.66 (dd, J=1.7, 6.9 Hz, 1H), 7.57 (d, J=8.6 Hz, 2H), 7.50 (ddd, J=2.0, 6.8, 9.0 Hz, 1H), 7.35-7.20 (m, 5H), 6.48 (d, J=9.0 Hz, 1H), 6.32 (dt, J=1.1, 6.8 Hz, 1H), 4.38 (d, J=5.9 Hz, 2H), 2.52 (s, 3H); MS (ES+) m/z 445.4 (M+1).

Sources & evidence

ORD record
ord-c04afa09250d40faa42fa29736d8d996
Source dataset
uspto-grants-2013_09
Patent number
US08541457B2

Reaction notes

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