Acetic Acid → N-{6-[4-(4-thiazole-2-ylmethylpiperazine-1-carbonyl)phenoxy]pyridin-3-yl}-4-trifluoromethyl-benzamide

HRID 884173Notes

Reaction equation

HRID 884173 reaction equation
Cl.Cl.[N:3]1([C:9]([C:11]2[CH:36]=[CH:35][C:14]([O:15][C:16]3[N:21]=[CH:20][C:19]([NH:22][C:23](=[O:34])[C:24]4[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=4)=[CH:18][CH:17]=3)=[CH:13][CH:12]=2)=[O:10])[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1.[CH:37]([C:39]1[S:40][CH:41]=[CH:42][N:43]=1)=O.C(N(CC)CC)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>ClCCCl>[S:40]1[CH:41]=[CH:42][N:43]=[C:39]1[CH2:37][N:6]1[CH2:7][CH2:8][N:3]([C:9]([C:11]2[CH:12]=[CH:13][C:14]([O:15][C:16]3[N:21]=[CH:20][C:19]([NH:22][C:23](=[O:34])[C:24]4[CH:29]=[CH:28][C:27]([C:30]([F:31])([F:32])[F:33])=[CH:26][CH:25]=4)=[CH:18][CH:17]=3)=[CH:35][CH:36]=2)=[O:10])[CH2:4][CH2:5]1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 8471TriethylamineHCID 27349031,3-Thiazole-2-carbaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 68525907N-{6-[4-(piperazine-1-carbonyl)phenoxy]pyridin-3-yl}-4-trifluoromethylbenzamide dihydrochloride

Product 1

HCID 68525584N-{6-[4-(4-thiazole-2-ylmethylpiperazine-1-carbonyl)phenoxy]pyridin-3-yl}-4-trifluoromethyl-benzamide

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a suspension of N-{6-[4-(piperazine-1-carbonyl)phenoxy]pyridin-3-yl}-4-trifluoromethyl-benzamide dihydrochloride (400 mg, 0.74 mmol) in 1,2-dichloroethane (20 mL) were added 2-formylthiazole (125 mg, 1.10 mmol) and triethylamine (0.21 mL, 1.50 mmol). After the resulting solution was stirred at room temperature for 30 minutes, sodium triacetyloxy borohydride (312 mg, 1.47 mmol) was added under ice cooling. The reaction mixture was stirred at the same temperature for 30 minutes and at room temperature for 1 hour. Acetic acid (0.085 mL, 1.48 mmol) was added to the reaction mixture, and stirred at room temperature for 17 hours. The reaction mixture was poured into ice water, and extracted with chloroform. The chloroform layer was washed with a saturated sodium bicarbonate solution and brine, and dried over anhydrous magnesium sulfate. A significant part of the solvent was evaporated. The white precipitate was then filtered off and washed with ethyl acetate, to thereby yield 293 mg of the title compound.

Workup

  1. stirringThe reaction mixture was stirred at the same temperature for 30 minutes and at room temperature for 1 hour
  2. stirringstirred at room temperature for 17 hours
  3. extractionextracted with chloroform
  4. washThe chloroform layer was washed with a saturated sodium bicarbonate solution and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customA significant part of the solvent was evaporated
  7. filtrationThe white precipitate was then filtered off
  8. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-fc007704b4b74bc096b4b827bcd5276a
Source dataset
uspto-grants-2012_08
Patent number
US08236826B2

Reaction notes

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