Benzoyl chloride → HCID 59369654, compound

HRID 45402Notes

Reaction equation

HRID 45402 reaction equation
[CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14]([NH2:16])=[N:13][C:12]=1[CH2:17][N:18]([CH2:21][CH3:22])[CH2:19][CH3:20])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:23](Cl)(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(N(CC)CC)C>O1CCCC1.CN(C)C1C=CN=CC=1>[C:23]([NH:16][C:14]1[S:15][C:11]([C:9]([NH:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:10])=[C:12]([CH2:17][N:18]([CH2:21][CH3:22])[CH2:19][CH3:20])[N:13]=1)(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 866425252-amino-N-benzyl-4-((diethylamino)methyl)thiazole-5-carboxamide

Product 1

HCID 59369654HCID 59369654, compoundYield 31.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-amino-4-diethylaminomethylthiazole-5-carboxylic acid benzylamide (0.052 g, 0.16 mmol) in tetrahydrofuran (5 mL) at 0° C. were added benzoyl chloride (0.04 mL, 0.34 mmol), 4-dimethylaminopyridine (catalytical amount) and triethylamine (0.3 mL, 2.10 mmol). The reaction mixture was allowed to warm to ambient temperature over 18 h then concentrated in vacuo. The crude product was purified by flash column chromatography eluting with methanol/dichloromethane (1/40 to 20/80) to afford the title compound (0.021 g); MS (ES+) m/z 423 (M+1).

Workup

  1. concentrationthen concentrated in vacuo
  2. customThe crude product was purified by flash column chromatography
  3. washeluting with methanol/dichloromethane (1/40 to 20/80)

Sources & evidence

ORD record
ord-184220bfbba34f049b568ce84464415f
Source dataset
uspto-grants-2013_09
Patent number
US08541457B2

Reaction notes

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