Water → HCID 10237511, compound

HRID 730287Notes

Reaction equation

HRID 730287 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:12][C:11]2[C:6](=[CH:7][C:8]([NH:13][C:14](=[O:27])/[CH:15]=[CH:16]/[C:17]3[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=3)=[CH:9][CH:10]=2)[NH:5][CH2:4]1.IC.[C:30]([O-])(O)=O.[Na+].O>CN(C=O)C>[OH:1][CH2:2][CH:3]1[CH2:12][C:11]2[C:6](=[CH:7][C:8]([NH:13][C:14](=[O:27])/[CH:15]=[CH:16]/[C:17]3[CH:18]=[CH:19][C:20]([C:23]([F:24])([F:25])[F:26])=[CH:21][CH:22]=3)=[CH:9][CH:10]=2)[N:5]([CH3:30])[CH2:4]1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 516892Sodium BicarbonateHCID 10193932HCID 10193932, compound

Product 1

HCID 10237511HCID 10237511, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of (2E)-N-[3-(hydroxymethyl)(7-1,2,3,4-tetrahydroquinolyl)]-3-[4-(trifluoromethyl)phenyl]prop-2-enamide, Example 87, (75 mg, 0.20 mmol), iodomethane (0.014 mL, 0.22 mmol, Aldrich) and NaHCO3 (84 mg, 1.0 mmol) in DMF (1.0 mL, Aldrich) was stirred for 4 h at room temperature. Water (5 mL) was added and the mixture was extracted with EtOAc (2×20 mL). The combined organic phases were washed with water (5 mL), satd NaCl (5 mL), dried over Na2SO4, filtered and concentrated in vacuo. Purification by silica gel chromatography (60% EtOAc/CH2Cl2) provided the title product as a white solid. MP 167-169° C. MS (ESI, pos. ion) m/z: 391 (M+1).

Workup

  1. extractionthe mixture was extracted with EtOAc (2×20 mL)
  2. washThe combined organic phases were washed with water (5 mL), satd NaCl (5 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by silica gel chromatography (60% EtOAc/CH2Cl2)

Sources & evidence

ORD record
ord-c9216c9bf7534855ad0e6458ebc78acf
Source dataset
uspto-grants-2009_09
Patent number
US07582657B2

Reaction notes

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