1,2-Dichloroethane → HCID 58413108, compound

HRID 240620Notes

Reaction equation

HRID 240620 reaction equation
C(Cl)CCl.[C:5]([O:9][C:10]([N:12]1[CH2:17][CH2:16][CH2:15][C@H:14]([O:18][C:19]2[CH:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:22]=[CH:21][C:20]=2[NH:29][C:30]2[C:31]3[C:38]([CH3:39])=[C:37]([C:40]([OH:42])=O)[S:36][C:32]=3[N:33]=[CH:34][N:35]=2)[CH2:13]1)=[O:11])([CH3:8])([CH3:7])[CH3:6].O[N:44]1C(=O)CCC1=O>CN(C=O)C.CCOC(C)=O>[C:5]([O:9][C:10]([N:12]1[CH2:17][CH2:16][CH2:15][C@H:14]([O:18][C:19]2[CH:24]=[C:23]([C:25]([F:26])([F:27])[F:28])[CH:22]=[CH:21][C:20]=2[NH:29][C:30]2[C:31]3[C:38]([CH3:39])=[C:37]([C:40]([NH2:44])=[O:42])[S:36][C:32]=3[N:33]=[CH:34][N:35]=2)[CH2:13]1)=[O:11])([CH3:6])([CH3:7])[CH3:8]

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 80170N-HydroxysuccinimideHCID 58413197HCID 58413197, compound

Product 1

HCID 58413108HCID 58413108, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

EDC (74 mg) added to a mixture of the 4-[2-((S)-1-tert-butoxycarbonyl-piperidin-3-yloxy)-4-trifluoromethyl-phenylamino]-5-methyl-thieno[2,3-d]pyrimidine-6-carboxylic acid (177 mg) and N-hydroxysuccinimide (55 mg) in DMF (4 ml). The reaction mixture was stirred at room temperature overnight. The reaction was diluted with EtOAc and washed with water and brine. The organics were passed through a hydrophobic frit and the solvent was evaporated. The residue was dissolved in DMF (2 ml) and ammonia in methanol (2 ml) was added. The reaction was stirred for 1 h. Further ammonia in methanol (2 ml) was added and the reaction was stirred again. After 30 min the reaction was diluted with EtOAc and washed with water and brine.

Workup

  1. washwashed with water and brine
  2. customthe solvent was evaporated
  3. dissolutionThe residue was dissolved in DMF (2 ml)
  4. additionammonia in methanol (2 ml) was added
  5. stirringThe reaction was stirred for 1 h
  6. additionFurther ammonia in methanol (2 ml) was added
  7. stirringthe reaction was stirred again
  8. additionAfter 30 min the reaction was diluted with EtOAc
  9. washwashed with water and brine

Sources & evidence

ORD record
ord-b0bd1e6684894ca6be0f21c75244040e
Source dataset
uspto-grants-2014_02
Patent number
US08648068B2

Reaction notes

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