1,2-Dichloroethane → HCID 178429336, compound

HRID 406086Notes

Reaction equation

HRID 406086 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](O)=[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][C@H:30]([OH:33])[CH2:29][CH2:28]2)[CH:7]=1.O[N:35]1C(=O)C[CH2:37][C:36]1=O.[CH3:42][N:43]([CH:45]=O)[CH3:44]>CCOC(C)=O>[CH3:42][N:43]([CH3:44])[CH2:45][CH2:37][CH2:36][NH:35][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[CH2:28][CH2:29][C@H:30]([OH:33])[CH2:31][CH2:32]3)[C:14]=2[C:21]=1[CH3:22])=[O:24]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 6228DimethylformamideHCID 80170N-HydroxysuccinimideHCID 178429620HCID 178429620, compound

Product 1

HCID 178429336HCID 178429336, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

0.072 g EDC were added to a mixture of 0.13 g 4-[4-fluoro-2-(trans-4-hydroxycyclohexyloxy)-phenylamino]-5-methyl-thieno[2,3-d]pyrimidine-6-carboxylic acid and 0.054 g N-Hydroxysuccinimide in DMF (2 ml). The reaction mixture was stirred at rt overnight then diluted with EtOAc and washed with water and brine (2×). The organic phase was passed through a hydrophobic frit and evaporated. The residue was treated with 2 ml DMF and 213 μl 3-dimethylaminopropylamine were added. The mixture was stirred at rt for 40 minutes and then diluted with EtOAc and washed with water and brine (2×). The organic phase was dried with MgSO4 and passed through a hydrophobic frit.

Workup

  1. washwashed with water and brine (2×)
  2. customevaporated
  3. additionThe residue was treated with 2 ml DMF and 213 μl 3-dimethylaminopropylamine
  4. additionwere added
  5. stirringThe mixture was stirred at rt for 40 minutes
  6. additiondiluted with EtOAc
  7. washwashed with water and brine (2×)
  8. dry with materialThe organic phase was dried with MgSO4

Sources & evidence

ORD record
ord-e45d692644494ca19a0c20ce8241dda1
Source dataset
uspto-grants-2014_06
Patent number
US08754079B2

Reaction notes

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