3-(Trifluoromethyl)benzoyl chloride → N-(3-cyano-4-thiophen-2-yl-6,7,8,9-tetrahydro-5H-1-thia-10-aza-cyclohepta[f]inden-2-yl)-3-trifluoromethyl-benzamide

HRID 1991465Notes

Reaction equation

HRID 1991465 reaction equation
[NH2:1][C:2]1[S:10][C:9]2[N:8]=[C:7]3[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:6]3=[C:5]([C:16]3[S:17][CH:18]=[CH:19][CH:20]=3)[C:4]=2[C:3]=1[C:21]#[N:22].[F:23][C:24]([F:35])([F:34])[C:25]1[CH:26]=[C:27]([CH:31]=[CH:32][CH:33]=1)[C:28](Cl)=[O:29]>CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[C:21]([C:3]1[C:4]2[C:5]([C:16]3[S:17][CH:18]=[CH:19][CH:20]=3)=[C:6]3[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][C:7]3=[N:8][C:9]=2[S:10][C:2]=1[NH:1][C:28](=[O:29])[C:27]1[CH:31]=[CH:32][CH:33]=[C:25]([C:24]([F:23])([F:34])[F:35])[CH:26]=1)#[N:22]

Participants

5

Reactant 2

HCID 752573-(Trifluoromethyl)benzoyl chlorideHCID 59129737HCID 59129737, compound

Product 1

HCID 11691779N-(3-cyano-4-thiophen-2-yl-6,7,8,9-tetrahydro-5H-1-thia-10-aza-cyclohepta[f]inden-2-yl)-3-trifluoromethyl-benzamideYield 26%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

A mixture of 2-amino-4-thiophen-2-yl-6,7,8,9-tetrahydro-5H-1-thia-10-aza-cyclohepta[f]indene-3-carbonitrile, prepared using the chemistry described in Example 1G (100 mg, 0.31 mmol), 3-trifluoromethyl-benzoyl chloride (77 mg, 0.37 mmol) and a catalytic amount of DMAP in pyridine (20 mL) was heated under reflux for one day. After concentration, the residue was partitioned between EtOAc and H2O. The organic layer was washed with brine, dried over MgSO4 and concentrated. The residue was purified by chromatography to give N-(3-cyano-4-thiophen-2-yl-6,7,8,9-tetrahydro-5H-1-thia-10-aza-cyclohepta[f]inden-2-yl)-3-trifluoromethyl-benzamide (40 mg, 26%).

Workup

  1. customprepared
  2. temperatureunder reflux for one day
  3. concentrationAfter concentration
  4. customthe residue was partitioned between EtOAc and H2O
  5. washThe organic layer was washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-9ca050d37f244b568b7890edec47951d
Source dataset
uspto-grants-2010_01
Patent number
US07645881B2

Reaction notes

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