Water → HCID 11998771, compound

HRID 1178339Notes

Reaction equation

HRID 1178339 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@@:9]([NH:38][CH3:39])([CH2:20][CH2:21][N:22]2[CH2:27][CH2:26][C:25]3([C:36]4[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=4)[CH2:30][C:29](=[O:37])[NH:28]3)[CH2:24][CH2:23]2)[CH2:10][N:11]([CH3:19])[C:12](=[O:18])[CH2:13][C:14]([F:17])([F:16])[F:15])[CH:5]=[CH:6][C:7]=1[Cl:8].C(N(CC)CC)C.[C:47](Cl)(=[O:54])[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1.O>C(#N)C>[F:16][C:14]([F:15])([F:17])[CH2:13][C:12]([N:11]([CH2:10][C@@:9]([N:38]([CH3:39])[C:47](=[O:54])[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)([C:4]1[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=1)[CH2:20][CH2:21][N:22]1[CH2:23][CH2:24][C:25]2([C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[CH2:30][C:29](=[O:37])[NH:28]2)[CH2:26][CH2:27]1)[CH3:19])=[O:18]

Participants

6

Reactant 4

HCID 962WaterHCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 58696254HCID 58696254, compound

Product 1

HCID 11998771HCID 11998771, compoundYield 85.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N-{2-(S)-(3,4-Dichlorophenyl)-2-methylamino-4-[3-oxo-3,4-dihydro-2H-spiro(isoquinoline-1,4′-piperidin)-1′-yl]butyl}-3,3,3-trifluoro-N-methylpropanamide (440 mg) was dissolved in acetonitrile (5 mL). Under cooling with ice, triethylamine (314 μL) and benzoyl chloride (174 μL) were added thereto, and the mixture was stirred for 1 hour at the same temperature. Water was added to the reaction mixture, and the resultant mixture was extracted with ethyl acetate, sequentially washed with 0.5N aqueous hydrochloric acid, water, saturated aqueous sodium bicarbonate, and saturated brine, and dried over sodium sulfate anhydrate. The solvent was concentrated under reduced pressure, and the residue was purified through silica gel column chromatography (n-hexane ethyl acetate=1:1→ethyl acetate→ethyl acetate:methanol=10:1), to thereby give the title compound (442 mg, 85.5%) as white powder.

Workup

  1. additionwere added
  2. extractionthe resultant mixture was extracted with ethyl acetate
  3. washsequentially washed with 0.5N aqueous hydrochloric acid, water, saturated aqueous sodium bicarbonate, and saturated brine
  4. dry with materialdried over sodium sulfate anhydrate
  5. concentrationThe solvent was concentrated under reduced pressure
  6. customthe residue was purified through silica gel column chromatography (n-hexane ethyl acetate=1:1→ethyl acetate→ethyl acetate:methanol=10:1)

Sources & evidence

ORD record
ord-cd110ab378bf4b74a64f6717a52ce17c
Source dataset
uspto-grants-2007_10
Patent number
US07276511B2

Reaction notes

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