Dimethylformamide → HCID 20651220, compound

HRID 1976256Notes

Reaction equation

HRID 1976256 reaction equation
[C:1]1([C:7]2[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=2[C:9]([OH:11])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(Cl)(Cl)=O.CN(C)C=O.[NH2:25][C:26]1[CH:49]=[CH:48][C:29]([C:30]([N:32]2[C:38]3[CH:39]=[CH:40][CH:41]=[CH:42][C:37]=3[S:36](=[O:44])(=[O:43])[N:35]3[CH2:45][CH2:46][CH2:47][C@H:34]3[CH2:33]2)=[O:31])=[CH:28][CH:27]=1>O1CCCC1.ClCCl.C(Cl)(Cl)Cl.CO.N1C=CC=CC=1>[C:1]1([C:7]2[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=2[C:9]([NH:25][C:26]2[CH:27]=[CH:28][C:29]([C:30]([N:32]3[C:38]4[CH:39]=[CH:40][CH:41]=[CH:42][C:37]=4[S:36](=[O:44])(=[O:43])[N:35]4[CH2:45][CH2:46][CH2:47][C@H:34]4[CH2:33]3)=[O:31])=[CH:48][CH:49]=2)=[O:11])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

9

Reactant 4

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 70357o-Phenylbenzoic acidHCID 20651221HCID 20651221, compound

Product 1

HCID 20651220HCID 20651220, compoundYield 22.6%

Reagents, catalysts & solvents 4

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolventHCID 21584188Chloroform methanolSolvent

Procedure

To a solution of 2-phenyl benzoic acid (0.1 g) in tetrahydrofuran (2 ml), there was added, with ice-cooling, 0.075 g of thionyl chloride and a catalytic amount of N,N-dimethylformamide and the mixture was heated under reflux for 2 hours. After concentration of the reaction solution, the resulting acid chloride was dissolved in 3 ml of dichloromethane and the resulting solution was dropwise added to a solution of (11aS)-10-(4-aminobenzoyl)-1,2,3,10,11,11a-hexahydro-pyrrolo[1,2-b][1,2,5]benzothiadiazepin-5,5-dioxide (0.15 g) prepared in Reference Example 37 and pyridine (0.05 g) in dichloromethane (3 ml) at room temperature for 15 minutes. After stirring the reaction solution at room temperature for 3 hours, it was poured into ice water and then extracted with ethyl acetate. The resulting organic phase was washed with water and dried over anhydrous magnesium sulfate. After concentration of the organic phase, the resulting residue was subjected to silica gel column chromatography and then eluted with chloroform/methanol (49/1) to thus give 0.05 g (yield 22.6%) of the title compound.

Workup

  1. temperaturecooling
  2. temperatureunder reflux for 2 hours
  3. extractionextracted with ethyl acetate
  4. washThe resulting organic phase was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate

Sources & evidence

ORD record
ord-9e9472812c854092ae9fb7b5eb436b79
Source dataset
uspto-grants-2001_05
Patent number
US06225306B1

Reaction notes

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