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

HRID 1640223ノート

反応式

HRID 1640223 の反応式
[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]

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 31374Dimethylacetamide溶媒HCID 22717425N,N-dimethylacetamide 1-methyl-2-pyrrolidone溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-bd9c7fa1a4ca48d8972d5e2531e847b6
出典データセット
uspto-grants-2012_02
特許番号
US08110687B2

反応ノート

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