Sodium hydride → 2-(4-Benzylbenzamido)-N-ethyl-4-methylthiazole-5-carboxamide

HRID 45394Notes

Reaction equation

HRID 45394 reaction equation
[NH2:1][C:2]1[S:3][C:4]([C:8]([NH:10][CH2:11][CH3:12])=[O:9])=[C:5]([CH3:7])[N:6]=1.[H-].[Na+].[CH2:15]([C:22]1[CH:30]=[CH:29][C:25]([C:26](Cl)=[O:27])=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>ClCCl>[CH2:15]([C:22]1[CH:23]=[CH:24][C:25]([C:26]([NH:1][C:2]2[S:3][C:4]([C:8]([NH:10][CH2:11][CH3:12])=[O:9])=[C:5]([CH3:7])[N:6]=2)=[O:27])=[CH:29][CH:30]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 212853564-Benzylbenzoyl chlorideHCID 62792171HCID 62792171, compound

Product 1

HCID 593696572-(4-Benzylbenzamido)-N-ethyl-4-methylthiazole-5-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-amino-N-ethyl-4-methylthiazole-5-carboxamide (0.17 g, 0.93 mmol) in dichloromethane (2 mL) at −78° C. was added sodium hydride (excess) followed by the addition of 4-benzylbenzoyl chloride (1 equiv of 0.5 M in N,N-dimethylformamide). The reaction was allowed to warm to ambient temperature over 18 h then concentrated in vacuo. The crude product was purified by preparative HPLC (acetone/water gradient) to afford the title compound (0.005 g); 1H NMR (CD3OD, 400 MHz) δ 7.90 (d, J=8.6 Hz, 2H), 7.35 (d, J=8.1 Hz, 2H), 7.27-7.13 (m, 5H), 4.03 (s, 2H), 3.32 (q, J=7.6 Hz, 2H), 2.50 (s, 3H), 1.17 (t, J=7.6 Hz, 3H); MS (ES+) m/z 380 (M+1).

Workup

  1. concentrationthen concentrated in vacuo
  2. customThe crude product was purified by preparative HPLC (acetone/water gradient)

Sources & evidence

ORD record
ord-5c78766990cf4a70a64f95402e70f282
Source dataset
uspto-grants-2013_09
Patent number
US08541457B2

Reaction notes

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