HCID 11554399, compound → HCID 11675110, compound

HRID 1441934Notes

Reaction equation

HRID 1441934 reaction equation
C([N:8]1[C:17]2[C:12](=[CH:13][C:14]([O:18][C:19](=[O:32])[NH:20][C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[C:23]([C:28]([F:31])([F:30])[F:29])[CH:22]=3)=[CH:15][CH:16]=2)[CH2:11][CH2:10][CH2:9]1)C1C=CC=CC=1.[H][H]>C(O)C.[Pd]>[NH:8]1[C:17]2[C:12](=[CH:13][C:14]([O:18][C:19](=[O:32])[NH:20][C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[C:23]([C:28]([F:29])([F:30])[F:31])[CH:22]=3)=[CH:15][CH:16]=2)[CH2:11][CH2:10][CH2:9]1

Participants

5

Reactant 2

HCID 11554399HCID 11554399, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 11675110HCID 11675110, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A nitrogen flushed mixture of 4-chloro-3-trifluoromethyl-phenyl-carbamic acid 1-benzyl-1, 2, 3, 4-tetrahydro-quinolin-6-yl ester (0.23 g. ½ mmol) and 5% Pd—C (0.02 g.) in absolute ethanol (20 ml) was shaken in a par apparatus at room temperature (38° C.) under 50 psi pressure of hydrogen for 5 hours. Pd—C was then discarded through filtration. The reaction mixture was concentrated under reduced pressure and the residue was washed dichloromethane (2×3 ml) to give 2e; yield: 0.16 g. (86.4%), m.p.: 150° C., C17H14ClF3N2O2; 1H NMR δ ppm (DMSO-d6): 1.89-1.95 (m, 2H.), 2.76 (t, 2H), 3.28 (t, 2H), 6.44-6.49 (m, 1H), 6.72-6.75 (m, 2H), 7.37-8.0 (m, 2H),10.14 (bs, 1H); IR vmax (KBr) (cm−1): 661, 698, 769, 796, 819, 892, 944, 1023, 1072, 1147, 1217, 1290, 1347, 1384, 1424, 1450, 1506, 1599, 1707, 1740, 2364, 2489, 2837, 2950, 3359, 3773, 3888.

Workup

  1. customA nitrogen flushed
  2. filtrationPd—C was then discarded through filtration
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. washthe residue was washed dichloromethane (2×3 ml)

Sources & evidence

ORD record
ord-c9f7cc20433546d79d4b4e2dee5575bc
Source dataset
uspto-grants-2010_02
Patent number
US07655801B2

Reaction notes

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