N-(4-(2-(1-Isopropyl-1,2,3,6-tetrahydropyridin-4-yl)-6-(4-(trifluoromethyl)-phenyl)pyrimidin-4-yloxy)benzo[d]thiazol-2-yl)acetamide → N-(4-(2-(1-Isopropylpiperidin-4-yl)-6-(4-(trifluoromethyl)phenyl)pyrimidin-4-yloxy)benzo[d]thiazol-2-yl)acetamide

HRID 2056700Notes

Reaction equation

HRID 2056700 reaction equation
[CH:1]([N:4]1[CH2:9][CH:8]=[C:7]([C:10]2[N:15]=[C:14]([O:16][C:17]3[C:22]4[N:23]=[C:24]([NH:26][C:27](=[O:29])[CH3:28])[S:25][C:21]=4[CH:20]=[CH:19][CH:18]=3)[CH:13]=[C:12]([C:30]3[CH:35]=[CH:34][C:33]([C:36]([F:39])([F:38])[F:37])=[CH:32][CH:31]=3)[N:11]=2)[CH2:6][CH2:5]1)([CH3:3])[CH3:2]>C(O)CCC.[OH-].[Pd+2].[OH-]>[CH:1]([N:4]1[CH2:9][CH2:8][CH:7]([C:10]2[N:15]=[C:14]([O:16][C:17]3[C:22]4[N:23]=[C:24]([NH:26][C:27](=[O:29])[CH3:28])[S:25][C:21]=4[CH:20]=[CH:19][CH:18]=3)[CH:13]=[C:12]([C:30]3[CH:35]=[CH:34][C:33]([C:36]([F:38])([F:39])[F:37])=[CH:32][CH:31]=3)[N:11]=2)[CH2:6][CH2:5]1)([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 11599284N-(4-(2-(1-Isopropyl-1,2,3,6-tetrahydropyridin-4-yl)-6-(4-(trifluoromethyl)-phenyl)pyrimidin-4-yloxy)benzo[d]thiazol-2-yl)acetamide

Product 1

HCID 11678448N-(4-(2-(1-Isopropylpiperidin-4-yl)-6-(4-(trifluoromethyl)phenyl)pyrimidin-4-yloxy)benzo[d]thiazol-2-yl)acetamide

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 2631-ButanolSolvent

Conditions

Temperature
120 °C

Procedure

To a mixture of N-(4-(2-(1-isopropyl-1,2,3,6-tetrahydropyridin-4-yl)-6-(4-(trifluoromethyl)phenyl)pyrimidin-4-yloxy)benzo[d]thiazol-2-yl)acetamide (100 mg, 0.18 mmol, Example 28), HCO2N44 (227 mg, 3.6 mmol, Aldrich) in butanol (2 mL) was added palladium hydroxide (8.3 mg, 0.016 mmol, 20 wt. % Pd (dry basis) on carbon, Aldrich), and the mixture was heated to 120° C. for 16 h with stirring under nitrogen atmosphere. After cooling to room temperature, the reaction mixture was filtered through Celite® pad. The filter cake was washed with MeOH and the combined filtrates were evaporated under reduced pressure. The residue was purified by silica gel column chromatography (7% MeOH/DCM) to provide the title compound as an amorphous solid. MS (ESI, pos. ion) m/z: 556 (M+1).

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe reaction mixture was filtered through Celite® pad
  3. washThe filter cake was washed with MeOH
  4. customthe combined filtrates were evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (7% MeOH/DCM)

Sources & evidence

ORD record
ord-157a9a8ab0b540eabab7b9b0ea1fdd22
Source dataset
uspto-grants-2008_02
Patent number
US07335672B2

Reaction notes

Loading…