4-Fluorobenzoyl chloride → HCID 86703390, compound

HRID 512559Notes

Reaction equation

HRID 512559 reaction equation
[NH2:1][C:2]1[S:6][C:5]([NH:7][C:8]2[CH:17]=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=2)=[N:4][C:3]=1[C:18]([O:20][CH2:21][CH3:22])=[O:19].[F:23][C:24]1[CH:32]=[CH:31][C:27]([C:28](Cl)=[O:29])=[CH:26][CH:25]=1>N1C=CC=CC=1.CCOC(C)=O>[F:23][C:24]1[CH:32]=[CH:31][C:27]([C:28]([NH:1][C:2]2[S:6][C:5]([NH:7][C:8]3[CH:17]=[CH:16][C:15]4[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=4)[CH:9]=3)=[N:4][C:3]=2[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[O:29])=[CH:26][CH:25]=1

Participants

5

Reactant 2

HCID 678794-Fluorobenzoyl chlorideHCID 86703384Ethyl 5-amino-2-(naphthalen-2-ylamino)thiazole-4-carboxylate

Product 1

HCID 86703390HCID 86703390, compoundYield 59.5%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of ethyl 5-amino-2-(naphthalen-2-ylamino)thiazole-4-carboxylate (170 mg, 0.54 mmol) in pyridine (3 mL) was added 4-fluorobenzoyl chloride (0.09 mL, 0.81 mmol) at 0° C. The mixture was allowed to warm to rt, and stirred overnight. The reaction mixture was diluted with EtOAc, and washed with water. The organic layer was dried over Na2SO4 and concentrated in vacuo. The residue was triturated with EtOAc, and the resulting solids were collected by filtration to give 140 mg (59% Yield) of the titled compound.

Workup

  1. washwashed with water
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was triturated with EtOAc
  5. filtrationthe resulting solids were collected by filtration

Sources & evidence

ORD record
ord-ef97f668900746069d9103e11c23882b
Source dataset
uspto-grants-2015_08
Patent number
US09102637B2

Reaction notes

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