Dimethylformamide → HCID 24998578, compound

HRID 1253868Notes

Reaction equation

HRID 1253868 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([O:12]C)=O)=[CH:4][CH:3]=1.[F:14][C:15]([F:26])([F:25])[C:16]1[CH:17]=[C:18]([N:22]=[C:23]=[O:24])[CH:19]=[CH:20][CH:21]=1.C([O-])(O)=O.[Na+].[CH3:32][N:33]([CH:35]=O)C>CN(C1C=CN=CC=1)C>[CH:32]1[C:21]2[C:16](=[CH:17][C:18]([NH:22][C:10](=[O:12])[CH2:9][CH2:8][C:5]3[CH:4]=[CH:3][C:2]([NH:1][C:23]([NH:22][C:18]4[CH:19]=[CH:20][CH:21]=[C:16]([C:15]([F:25])([F:26])[F:14])[CH:17]=4)=[O:24])=[CH:7][CH:6]=3)=[CH:19][CH:20]=2)[CH:15]=[CH:35][N:33]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 94833-(Trifluoromethyl)phenyl isocyanateHCID 417374Methyl 3-(4-aminophenyl)propanoateHCID 516892Sodium Bicarbonate

Product 1

HCID 24998578HCID 24998578, compound

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

Steps one, three and four were performed as in Example 208. Step two is performed as follows: To methyl 3-(4-aminophenyl)propanoate in DMF is added DMAP and 3-trifluoromethylphenyl isocyanate and the solution was stirred at room temperature for 4 hours. The mixture was poured into NaHCO3 (sat), extracted with EtOAc, dried (Na2SO4), filtered and evaporated. The compound E210b was purified by flash chromatography.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated
  5. customThe compound E210b was purified by flash chromatography

Sources & evidence

ORD record
ord-bae3ea465a534da093a560b622fd35f5
Source dataset
uspto-grants-2013_06
Patent number
US08455513B2

Reaction notes

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