Veratroyl chloride → HCID 71060867, compound

HRID 1771135Notes

Reaction equation

HRID 1771135 reaction equation
[NH2:1][C:2]1[S:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[C:13]([NH2:15])=[O:14].[CH3:16][O:17][C:18]1[CH:19]=[C:20]([CH:24]=[CH:25][C:26]=1[O:27][CH3:28])[C:21](Cl)=[O:22].C1CCN2C(=NCCC2)CC1>CN1C(=O)CCC1>[CH3:16][O:17][C:18]1[CH:19]=[C:20]([CH:24]=[CH:25][C:26]=1[O:27][CH3:28])[C:21]([NH:1][C:2]1[S:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[C:13]([NH2:15])=[O:14])=[O:22]

Participants

5

Reactant 3

HCID 77070Veratroyl chlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 44122509HCID 44122509, compound

Product 1

HCID 71060867HCID 71060867, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent2×

Procedure

To a solution of 5-amino-2-phenyl-1,3-thiazole-4-carboxamide (0.3 g, 1.4 mmol) in NMP (1 mL) is added a solution of 3,4-dimethoxybenzoyl chloride (0.41 g, 2.0 mmol) in NMP (3 mL) followed by DBU (0.21 g, 1.4 mmol) and the mixture is stirred at reflux for 4 h. The resulting precipitate is collected by filtration, washed with NMP, acetonitrile, ethanol, ether to give 0.1 g (30%) of the title compound. This is further purified by reverse-phase HPLC: 1H NMR (400 MHz, DMSO-d6) δ [ppm]3.9 (s, 6H); 7.2 (d, J=8.3 Hz, 1H); 7.5 (m, 5H); 8.0 (m, 3H); 8.1 (s, 1H); 12.7 (s, 1H).

Workup

  1. temperatureat reflux for 4 h
  2. filtrationThe resulting precipitate is collected by filtration
  3. washwashed with NMP, acetonitrile, ethanol, ether

Sources & evidence

ORD record
ord-1501066a4b43476d919762cabb6f374f
Source dataset
uspto-grants-2016_02
Patent number
US09249114B2

Reaction notes

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