Diisopropylamine → HCID 69519748, compound

HRID 1179992Notes

Reaction equation

HRID 1179992 reaction equation
Cl.Cl.[CH:3]1([N:9]([CH3:16])[CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.Cl[C:18]([O:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][C:28]2[CH:33]=[CH:32][C:31]([C:34]([F:37])([F:36])[F:35])=[CH:30][N:29]=2)=[CH:23][CH:22]=1)=[O:19].C(NC(C)C)(C)C>CN(C)C=O.O1CCCC1>[F:36][C:34]([F:35])([F:37])[C:31]1[CH:32]=[CH:33][C:28]([O:27][C:24]2[CH:25]=[CH:26][C:21]([O:20][C:18]([N:13]3[CH2:12][CH2:11][CH:10]([N:9]([CH:3]4[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]4)[CH3:16])[CH2:15][CH2:14]3)=[O:19])=[CH:22][CH:23]=2)=[N:29][CH:30]=1

Participants

5

Reactant 3

HCID 7912DiisopropylamineHCID 220477624-(5-Trifluoromethylpyridin-2-yloxy)-phenyl chloroformateHCID 56831596HCID 56831596, compound

Product 1

HCID 69519748HCID 69519748, compound

Reagents, catalysts & solvents 1

HCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Procedure

The title product was prepared from cyclohexyl-methyl-piperidin-4-yl-amine, dihydrochloride and 4-(5-trifluoromethyl-pyridin-2-yloxy)-phenyl chloroformate, 2 equivalent of diisopropylamine; dimethylformamide/tetrahydrofuran (2:1). The reaction mixture was evaporated to dryness and the crude product extracted with ethyl acetate from an aqueous HCl solution saturated with sodium chloride, pH 1-2. The title product was crystallized from ethyl acetate during evaporation of the solvent, filtered and dried in vacuum (45%, white crystals). HPLC-MS m/z=478.2 (M+1), Rt: 3.10 min.

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. extractionthe crude product extracted with ethyl acetate from an aqueous HCl solution saturated with sodium chloride, pH 1-2
  3. customThe title product was crystallized from ethyl acetate during evaporation of the solvent
  4. filtrationfiltered
  5. customdried in vacuum (45%, white crystals)

Sources & evidence

ORD record
ord-c8d2e578ba81478487c8a435aba19f08
Source dataset
uspto-grants-2007_10
Patent number
US07279470B2

Reaction notes

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