1,2-Dichloroethane → HCID 58421683, compound

HRID 406075Notes

Reaction equation

HRID 406075 reaction equation
C(Cl)CCl.[F:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13]2[C:14]3[C:21]([CH3:22])=[C:20]([C:23]([OH:25])=[O:24])[S:19][C:15]=3[N:16]=[CH:17][N:18]=2)=[C:8]([O:26][C@H:27]2[CH2:32][CH2:31][CH2:30][CH2:29][C@@H:28]2[O:33][CH3:34])[CH:7]=1.O[N:36]1[C:40](=[O:41])[CH2:39][CH2:38][C:37]1=[O:42]>CN(C=O)C.CCOC(C)=O>[O:42]=[C:37]1[CH2:38][CH2:39][C:40](=[O:41])[N:36]1[O:24][C:23]([C:20]1[S:19][C:15]2[N:16]=[CH:17][N:18]=[C:13]([NH:12][C:9]3[CH:10]=[CH:11][C:6]([F:5])=[CH:7][C:8]=3[O:26][C@H:27]3[CH2:32][CH2:31][CH2:30][CH2:29][C@@H:28]3[O:33][CH3:34])[C:14]=2[C:21]=1[CH3:22])=[O:25]

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 80170N-HydroxysuccinimideHCID 58421745HCID 58421745, compound

Product 1

HCID 58421683HCID 58421683, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

EDC (53 mg, 0.28 mmol) was added to a mixture of 0.100 g 4-[4-fluoro-2-((1S,2S)-2-methoxy-cyclohexyloxy)-phenylamino]-5-methyl-thieno[2,3-d]pyrimidine-6-carboxylic acid (cpd.42.2) and 0.040 g N-hydroxysuccinimide in 1 ml DMF. And stirred at rt overnight. The reaction mixture was diluted with EtOAc and washed with water and brine. The organic layer was passed through a hydrophobic frit and concentrated.

Workup

  1. washwashed with water and brine
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-6972c0a3579e4be5b0e428055faff6ae
Source dataset
uspto-grants-2014_06
Patent number
US08754079B2

Reaction notes

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