Dichloromethane → HCID 57732141, compound

HRID 401750Notes

Reaction equation

HRID 401750 reaction equation
C(O)(C(F)(F)F)=O.COC1C=C(OC)C=CC=1C[N:13]([C:37]1[S:38][CH:39]=[CH:40][N:41]=1)[S:14]([C:17]1[CH:36]=[CH:35][C:20]([C:21]([NH:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=2)=[O:22])=[CH:19][N:18]=1)(=[O:16])=[O:15].C(Cl)Cl.C(N(CC)CC)C>CCOCC>[S:38]1[CH:39]=[CH:40][N:41]=[C:37]1[NH:13][S:14]([C:17]1[CH:36]=[CH:35][C:20]([C:21]([NH:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([C:31]([F:33])([F:34])[F:32])=[CH:27][CH:26]=2)=[O:22])=[CH:19][N:18]=1)(=[O:15])=[O:16]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acid2×HCID 8471TriethylamineHCID 57732179HCID 57732179, compound

Product 1

HCID 57732141HCID 57732141, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

TFA (750 μL, 9.7 mmol) was added to a solution of 6-{[(2,4-dimethoxybenzyl)(1,3-thiazol-2-yl)amino]sulfonyl}-N-[4-(trifluoromethyl)benzyl]nicotinamide (Preparation 88, 1.15 g, 1.94 mmol) in methylene chloride (12 mL, 180 mmol). After 30 min, the reaction mixture was diluted with ether. Triethylamine was added until basic to neutralize the residual TFA. Celite was added, and the mixture was concentrated in vacuo. The residue was purified on the Isco (120 g SiO2 cartridge, chloroform to 12% MeOH in chloroform). The appropriate fractions were concentrated in vacuo. The residue was treated with acetonitrile, generating a white precipitate. The volume was reduced in vacuo, and the solids were collected via filtration, washing with acetonitrile. The off-white product was dried under vacuum (428 mg, 47%).

Workup

  1. additionCelite was added
  2. concentrationthe mixture was concentrated in vacuo
  3. customThe residue was purified on the Isco (120 g SiO2 cartridge, chloroform to 12% MeOH in chloroform)
  4. concentrationThe appropriate fractions were concentrated in vacuo
  5. additionThe residue was treated with acetonitrile
  6. filtrationthe solids were collected via filtration
  7. washwashing with acetonitrile
  8. customThe off-white product was dried under vacuum (428 mg, 47%)

Sources & evidence

ORD record
ord-e69d03092a4043dabffe6fe5c6cc1c47
Source dataset
uspto-grants-2014_06
Patent number
US08741934B2

Reaction notes

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