N-Aminomorpholine → 6-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-N-morpholin-4-yl-nicotinamide

HRID 1516194노트

반응식

HRID 1516194 반응식
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[CH2:13][O:14][C:15]1[CH:23]=[CH:22][C:18]([C:19]([OH:21])=O)=[CH:17][N:16]=1.[NH2:24][N:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>CN(C=O)C>[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:3]=1[CH2:13][O:14][C:15]1[CH:23]=[CH:22][C:18]([C:19]([NH:24][N:25]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)=[O:21])=[CH:17][N:16]=1

참가 물질

6

반응물 4

HCID 20315N-AminomorpholineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 665992136-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-nicotinic acid

생성물 1

HCID 498009756-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-N-morpholin-4-yl-nicotinamide수율 40%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a stirred solution of 6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-nicotinic acid (100 mg, 0.32 mmol) in DMF (5 mL) at room temperature under argon was added N-aminomorpholine (36 mg, 0.35 mmol), 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (0.114 g, 0.35 mmol) and N,N-diisopropylethylamine (208 mg, 1.6 mmol). After 15 h the reaction mixture was concentrated, diluted with water and extracted with ethyl acetate. The combined organic extracts were dried over sodium sulfate, filtered and concentrated. Purification by chromatography (silica, dichloromethane:methanol 1:0 to 97.5:2.5) afforded the title compound (50 mg, 40%) as a white solid. MS: m/e=395.1 [M+H]+.

후처리

  1. concentrationAfter 15 h the reaction mixture was concentrated
  2. additiondiluted with water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic extracts were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by chromatography (silica, dichloromethane:methanol 1:0 to 97.5:2.5)

출처 및 근거

ORD 기록
ord-61168f36e94d43deaf1feca82ad20dde
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08227461B2

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