Triethylamine → Isoquinoline-1-carboxylic acid [2-((S)-2-imidazol-1-yl-1-pyridin-3-yl-ethoxy)-5-oxo-5,6,7,8-tetrahydro-naphthalen-1-yl]-amide

HRID 496430ノート

反応式

HRID 496430 の反応式
[NH2:1][C:2]1[C:11]([O:12][C@@H:13](C2C=CC=CC=2)[CH2:14][N:15]2[CH:19]=[CH:18][N:17]=[CH:16]2)=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][CH2:6][C:7]2=[O:26].[C:27]1([C:37]([OH:39])=O)[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:30]=[CH:29][N:28]=1.CN(C(ON1N=N[C:50]2[CH:51]=[CH:52][CH:53]=[N:54][C:49]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(CC)CC>C(Cl)Cl>[N:15]1([CH2:14][C@H:13]([C:52]2[CH:53]=[N:54][CH:49]=[CH:50][CH:51]=2)[O:12][C:11]2[CH:10]=[CH:9][C:8]3[C:7](=[O:26])[CH2:6][CH2:5][CH2:4][C:3]=3[C:2]=2[NH:1][C:37]([C:27]2[C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[CH:30]=[CH:29][N:28]=2)=[O:39])[CH:19]=[CH:18][N:17]=[CH:16]1

参加物

6

反応物 4

HCID 8471TriethylamineHCID 68092Isoquinoline-1-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 600298675-Amino-6-((S)-2-imidazol-1-yl-1-phenyl-ethoxy)-3,4-dihydro-2H-naphthalen-1-one

生成物 1

HCID 60029904Isoquinoline-1-carboxylic acid [2-((S)-2-imidazol-1-yl-1-pyridin-3-yl-ethoxy)-5-oxo-5,6,7,8-tetrahydro-naphthalen-1-yl]-amide収率 79%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a mixture of 5-amino-6-((S)-2-imidazol-1-yl-1-phenyl-ethoxy)-3,4-dihydro-2H-naphthalen-1-one (100 mg, 0.287 mmol), 1-isoquinoline carboxylic acid (60 mg, 0.344 mmol), and HATU (131 mg, 0.344 mmol) was added CH2Cl2 (3 mL) and Et3N (48 μL, 0.344 mmol). The reaction was stirred at RT for 5 h. The mixture was diluted with CH2Cl2 and washed with H2O, saturated aqueous NaHCO3 and brine, dried over Na2SO4, and concentrated to give a foam/oil. Purification by chromatography (SiO2, 5-8% MeOH/CH2Cl2) afforded the title compound as a foam (114 mg, 0.226 mmol, 79%). The structure was confirmed by NMR and mass spectrometry. MS m/z 504 (M++H).

後処理

  1. washwashed with H2O, saturated aqueous NaHCO3 and brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customto give a foam/oil
  5. customPurification by chromatography (SiO2, 5-8% MeOH/CH2Cl2)

出典と根拠

ORDレコード
ord-ea913423abb44ab2a9d6650e2c72d9e8
出典データセット
uspto-grants-2005_09
特許番号
US06943183B2

反応ノート

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