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Ammonium Chloride → N-(3,5-Bis-trifluoromethyl-benzyl)-N-methyl-6-morpholin-4-yl-4-phenoxy-nicotinamide

HRID 1358620
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HRID 1358620 반응식
[N:1]1([C:7]2[CH:15]=[C:14]([O:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:10]([C:11]([OH:13])=O)=[CH:9][N:8]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[F:23][C:24]([F:39])([F:38])[C:25]1[CH:26]=[C:27]([CH:31]=[C:32]([C:34]([F:37])([F:36])[F:35])[CH:33]=1)[CH2:28][NH:29][CH3:30].[Cl-].[NH4+]>CN(C1C=CN=CC=1)C.ClCCl.O>[F:23][C:24]([F:38])([F:39])[C:25]1[CH:26]=[C:27]([CH:31]=[C:32]([C:34]([F:37])([F:36])[F:35])[CH:33]=1)[CH2:28][N:29]([CH3:30])[C:11](=[O:13])[C:10]1[C:14]([O:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[CH:15][C:7]([N:1]2[CH2:2][CH2:3][O:4][CH2:5][CH2:6]2)=[N:8][CH:9]=1
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참가 물질

7

반응물 3

HCID 25517Ammonium ChlorideHCID 10956204{[3,5-Bis(trifluoromethyl)phenyl]methyl}(methyl)amineHCID 181853776-Morpholin-4-yl-4-phenoxy-nicotinic acid

생성물 1

HCID 9807285N-(3,5-Bis-trifluoromethyl-benzyl)-N-methyl-6-morpholin-4-yl-4-phenoxy-nicotinamide수율 84%

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine
촉매
HCID 962Water용매
HCID 6344Dichloromethane용매

실험 절차

A mixture of 46 mg (0.15 mmol) 6-morpholin-4-yl-4-phenoxy-nicotinic acid, 43 mg (0.17 mmol) (3,5-bis-trifluoromethyl-benzyl)-methylamine, 32 mg (0.17 mmol) 1-(3-diaminopropyl)-3-ethyl-carbodiimide hydrochloride and a catalytic amount of 4-(N,N-dimethylamino)-pyridine in 3 ml dichloromethane was stirred at room temperature over night. The reaction mixture was diluted with water, adjusted to pH 6 with saturated aqueous ammonium chloride solution and extracted with dichloromethane. The combined organic layers were washed with saturated aqueous sodium chloride solution, dried with sodium sulfate and concentrated. Flash column chromatography afforded 68 mg (83%) of the title compound as a white solid.

후처리

  1. extractionextracted with dichloromethane
  2. washThe combined organic layers were washed with saturated aqueous sodium chloride solution
  3. dry with materialdried with sodium sulfate
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-36182eeb80a94982b14cc0be3d519c26
출처 데이터셋
uspto-grants-2003_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06596773B2

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