Diisopropylethylamine → N-benzyl-2-(4-benzylbenzamido)-4-methylthiazole-5-carboxamide

HRID 45393Notes

Reaction equation

HRID 45393 reaction equation
[CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14]([NH2:16])=[N:13][C:12]=1[CH3:17])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.[CH2:27]([C:34]1[CH:42]=[CH:41][C:37]([C:38](O)=[O:39])=[CH:36][CH:35]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.F[P-](F)(F)(F)(F)F.C[N+](C)=C(N(C)C)ON1C2N=CC=CC=2N=N1>ClCCl>[CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14]([NH:16][C:38](=[O:39])[C:37]2[CH:36]=[CH:35][C:34]([CH2:27][C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)=[CH:42][CH:41]=2)=[N:13][C:12]=1[CH3:17])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 1364294-Benzylbenzoic acidHCID 210824N-Benzyl-2-imino-4-methyl-2,3-dihydro-1,3-thiazole-5-carboximidic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 59369673N-benzyl-2-(4-benzylbenzamido)-4-methylthiazole-5-carboxamideYield 3.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-amino-4-methyl-thiazole-5-carboxylic acid benzylamide (0.054 g, 0.22 mmol) and diisopropylethylamine (0.40 mL, 2.3 mmol) in dichloromethane (5 mL) was added 4-benzylbenzoic acid (0.057 g, 0.27 mmol), followed by the addition of N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (0.11 g, 0.28 mmol). The reaction was stirred at 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 (0.003 g); MS (ES+) m/z 442 (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-aac9ba002ade4956bd8a294454f824c1
Source dataset
uspto-grants-2013_09
Patent number
US08541457B2

Reaction notes

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