Dimethylformamide → HCID 25110359, compound

HRID 41122Notes

Reaction equation

HRID 41122 reaction equation
[C:1]1([C:7]2[CH:8]=[C:9]([C:16]([OH:18])=O)[S:10][C:11]=2[C:12]([F:15])([F:14])[F:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC[N:21]=[C:22]=[N:23]CCCN(C)C.[CH:30]1[CH:31]=[CH:32][C:33]2N(O)N=[N:36][C:34]=2C=1.[CH3:40]N(C=O)C>>[CH3:40][C:33]1[CH:34]=[N:36][CH:30]=[CH:31][C:32]=1[C:22]1[N:23]=[C:16]([C:9]2[S:10][C:11]([C:12]([F:13])([F:14])[F:15])=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH:8]=2)[O:18][N:21]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 27833724-Phenyl-5-(trifluoromethyl)thiophene-2-carboxylic acid

Product 1

HCID 25110359HCID 25110359, compoundYield 56.6%

Procedure

To a solution of 4-phenyl-5-(trifluoromethyl)-2-thiophenecarboxylic acid (200 mg, 0.735 mmol) in DMF were added under nitrogen atmosphere EDCI (183 mg, 0.95 mmol) and HOBt (129 mg, 0.95 mmol). The reaction was stirred at room temperature for 30 min followed by addition of N-hydroxyimidamide (143 mg, 0.95 mmol), the reaction was stirred for 30 min at room temperature followed by 16 h at 95° C. The reaction was concentrated under reduced pressure. The crude was diluted with EtOAc (80 mL) and washed with a saturated solution of NaHCO3 (2×50 ml). The organic phase was dried over Na2SO4 and concentrated under reduced pressure. The product was purified by column chromatography using CH2Cl2:MeOH (9:1) to yield 161 mg (56.6%) of the product. MS (EI) m/z: 412 (M+)

Workup

  1. stirringthe reaction was stirred for 30 min at room temperature
  2. waitfollowed by 16 h at 95° C
  3. concentrationThe reaction was concentrated under reduced pressure
  4. additionThe crude was diluted with EtOAc (80 mL)
  5. washwashed with a saturated solution of NaHCO3 (2×50 ml)
  6. dry with materialThe organic phase was dried over Na2SO4
  7. concentrationconcentrated under reduced pressure
  8. customThe product was purified by column chromatography

Sources & evidence

ORD record
ord-78095ca795b949849d03aefe0b6fc763
Source dataset
uspto-grants-2013_09
Patent number
US08530503B2

Reaction notes

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