Diisopropylethylamine → 4-({7-[(3-fluoro-4-methoxybenzoyl)amino]-5,6,7,8-tetrahydronaphthalen-2-yl}oxy)-N-methylpyridine-2-carboxamide

HRID 1640223노트

반응식

HRID 1640223 반응식
[NH2:1][CH:2]1[CH2:11][C:10]2[CH:9]=[C:8]([O:12][C:13]3[CH:18]=[CH:17][N:16]=[C:15]([C:19]([NH:21][CH3:22])=[O:20])[CH:14]=3)[CH:7]=[CH:6][C:5]=2[CH2:4][CH2:3]1.[F:23][C:24]1[CH:25]=[C:26]([CH:30]=[CH:31][C:32]=1[O:33][CH3:34])[C:27](O)=[O:28].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CC(N(C)C)=O.CC(N(C)C)=O.CN1C(=O)CCC1.O>[F:23][C:24]1[CH:25]=[C:26]([CH:30]=[CH:31][C:32]=1[O:33][CH3:34])[C:27]([NH:1][CH:2]1[CH2:11][C:10]2[CH:9]=[C:8]([O:12][C:13]3[CH:18]=[CH:17][N:16]=[C:15]([C:19]([NH:21][CH3:22])=[O:20])[CH:14]=3)[CH:7]=[CH:6][C:5]=2[CH2:4][CH2:3]1)=[O:28]

참가 물질

8

반응물 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 27334013-Fluoro-4-methoxybenzoic acidHCID 589024394-[(7-amino-5,6,7,8-tetrahydronaphthalen-2-yl)oxy]-N-methylpyridine-2-carboxamide

생성물 1

HCID 589024604-({7-[(3-fluoro-4-methoxybenzoyl)amino]-5,6,7,8-tetrahydronaphthalen-2-yl}oxy)-N-methylpyridine-2-carboxamide수율 70.1%

시약·촉매·용매 3

HCID 962Water용매HCID 31374Dimethylacetamide용매HCID 22717425N,N-dimethylacetamide 1-methyl-2-pyrrolidone용매

실험 절차

To a stirred solution of 4-[(7-amino-5,6,7,8-tetrahydronaphthalen-2-yl)oxy]-N-methylpyridine-2-carboxamide (25 mg) in DMA (1 mL) were added 3-fluoro-4-methoxybenzoic acid (16 mg, 0.094 mmol), DIPEA (26 μL), and a solution of TBTU (41 mg, 0.128 mmol) in DMA:NMP (1:1 v/v, 1 mL). The reaction mixture was allowed to stir at rt for 24 h. Water was added and the mixture was extracted with DCM. The organic solution was concentrated and purified by reverse phase HPLC to give 4-({7-[(3-fluoro-4-methoxybenzoyl)amino]-5,6,7,8-tetrahydronaphthalen-2-yl}oxy)-N-methylpyridine-2-carboxamide (26.5 mg, 70%). LCMS: (AA) ES+450.5.

후처리

  1. extractionthe mixture was extracted with DCM
  2. concentrationThe organic solution was concentrated
  3. custompurified by reverse phase HPLC

출처 및 근거

ORD 기록
ord-bd9c7fa1a4ca48d8972d5e2531e847b6
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08110687B2

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