4-Benzylbenzoyl chloride → 2-(4-Benzylbenzamido)-N-(2-cyanoethyl)-4-methylthiazole-5-carboxamide

HRID 45395Notes

Reaction equation

HRID 45395 reaction equation
[NH2:1][C:2]1[S:3][C:4]([C:8]([NH:10][CH2:11][CH2:12][C:13]#[N:14])=[O:9])=[C:5]([CH3:7])[N:6]=1.NC1SC(C(NCC)=O)=C(C)N=1.[CH2:27]([C:34]1[CH:42]=[CH:41][C:37]([C:38](Cl)=[O:39])=[CH:36][CH:35]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>>[CH2:27]([C:34]1[CH:35]=[CH:36][C:37]([C:38]([NH:1][C:2]2[S:3][C:4]([C:8]([NH:10][CH2:11][CH2:12][C:13]#[N:14])=[O:9])=[C:5]([CH3:7])[N:6]=2)=[O:39])=[CH:41][CH:42]=1)[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

4

Reactant 3

HCID 212853564-Benzylbenzoyl chlorideHCID 62792171HCID 62792171, compoundHCID 62793745HCID 62793745, compound

Product 1

HCID 593696902-(4-Benzylbenzamido)-N-(2-cyanoethyl)-4-methylthiazole-5-carboxamide

Procedure

Following the procedure as described in Example 20, making variation only as required to use 2-amino-N-(2-cyanoethyl)-4-methylthiazole-5-carboxamide to replace 2-amino-N-ethyl-4-methylthiazole-5-carboxamide to react with 4-benzylbenzoyl chloride, the title compound was obtained; 1H NMR (CD3OD, 400 MHz) δ 7.90 (d, J=8.1 Hz, 2H), 7.35 (d, J=8.6 Hz, 2H), 7.27-7.10 (m, 5H), 4.03 (s, 2H), 3.54 (t, J=6.6 Hz, 2H), 2.73 (t, J=6.6 Hz, 2H), 2.54 (s, 3H), 2.32 (s, 1H); MS (ES+) m/z 405 (M+1).

Sources & evidence

ORD record
ord-6b324a3b121d4621bfde6cc8a45a440e
Source dataset
uspto-grants-2013_09
Patent number
US08541457B2

Reaction notes

Loading…