1,2-Dichloroethane → 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

HRID 2056699Notes

Reaction equation

HRID 2056699 reaction equation
[NH:1]1[CH2:6][CH:5]=[C:4]([C:7]2[N:12]=[C:11]([O:13][C:14]3[C:19]4[N:20]=[C:21]([NH:23][C:24](=[O:26])[CH3:25])[S:22][C:18]=4[CH:17]=[CH:16][CH:15]=3)[CH:10]=[C:9]([C:27]3[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][CH:28]=3)[N:8]=2)[CH2:3][CH2:2]1.Cl[CH2:38][CH2:39]Cl.[C:41](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CC(O)=O.CC(C)=O.CN(C=O)C>[CH:38]([N:1]1[CH2:2][CH:3]=[C:4]([C:7]2[N:12]=[C:11]([O:13][C:14]3[C:19]4[N:20]=[C:21]([NH:23][C:24](=[O:26])[CH3:25])[S:22][C:18]=4[CH:17]=[CH:16][CH:15]=3)[CH:10]=[C:9]([C:27]3[CH:28]=[CH:29][C:30]([C:33]([F:34])([F:35])[F:36])=[CH:31][CH:32]=3)[N:8]=2)[CH2:5][CH2:6]1)([CH3:39])[CH3:41]

Participants

7

Reactant 3

HCID 111,2-DichloroethaneHCID 5049666Sodium triacetoxyborohydride2×HCID 11598707N-(4-(2-(1,2,3,6-tetrahydropyridin-4-yl)-6-(4-(trifluoromethyl)phenyl)pyrimidin-4-yloxy)benzo[d]thiazol-2-yl)acetamide

Product 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

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 180AcetoneSolvent2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of N-(4-(2-(1,2,3,6-tetrahydropyridin-4-yl)-6-(4-(trifluoromethyl)phenyl)pyrimidin-4-yloxy)benzo[d]thiazol-2-yl)acetamide (109 mg, 0.195 mmol, Example 27), acetone (1 mL), 1,2-dichloroethane (6 mL) and DMF (0.5 mL) was added AcOH (one drop), and the mixture was heated at 50° C. with stirring for 10 min. The reaction mixture was left to reach room temperature, sodium triacetoxyborohydride (127 mg, 0.6 mmol, Aldrich) was added, and the stirring was continued for 2 h at room temperature. After the addition of acetone (1 mL) and sodium triacetoxyborohydride (127 mg, 0.6 mmol), the reaction mixture was stirred at room temperature for 1 h and evaporated under reduced pressure. The yellow residue was treated with 1N NaOH (5 mL) and extracted with EtOAc (2×20 mL). The combined EtOAc extracts were dried over Na2SO4, filtered, and concentrated in vacuo. Purification of the residue by silica gel column chromatography (gradient 0.5-5% (2M NH3 in MeOH) in EtOAc) afforded the title compound as a pale-yellow amorphous solid. MS (ESI, pos. ion.) m/z: 554 (M+1).

Workup

  1. waitThe reaction mixture was left
  2. customto reach room temperature
  3. waitthe stirring was continued for 2 h at room temperature
  4. stirringthe reaction mixture was stirred at room temperature for 1 h
  5. customevaporated under reduced pressure
  6. additionThe yellow residue was treated with 1N NaOH (5 mL)
  7. extractionextracted with EtOAc (2×20 mL)
  8. dry with materialThe combined EtOAc extracts were dried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customPurification of the residue by silica gel column chromatography (gradient 0.5-5% (2M NH3 in MeOH) in EtOAc)

Sources & evidence

ORD record
ord-9bdcf3aaf13d4d559a9e0480e715b61d
Source dataset
uspto-grants-2008_02
Patent number
US07335672B2

Reaction notes

Loading…