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Water → N-[4-chloro-3-(trifluoromethyl)phenyl]-7-{[2-(4,5-dihydro-1H-imidazol-2-yl)-pyridin-4-yl]oxy}-1,2,3,4-tetrahydronaphthalene-2-carboxamide

HRID 1640167
ノート
印刷プレビュー

反応式

HRID 1640167 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([CH:11]2[CH2:20][CH2:19][C:18]3[C:13](=[CH:14][C:15]([OH:21])=[CH:16][CH:17]=3)[CH2:12]2)=[O:10])=[CH:4][C:3]=1[C:22]([F:25])([F:24])[F:23].Cl[C:27]1[CH:32]=[CH:31][N:30]=[C:29]([C:33]2[NH:34][CH2:35][CH2:36][N:37]=2)[CH:28]=1.C([O-])([O-])=O.[Cs+].[Cs+].O>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([CH:11]2[CH2:20][CH2:19][C:18]3[C:13](=[CH:14][C:15]([O:21][C:27]4[CH:32]=[CH:31][N:30]=[C:29]([C:33]5[NH:34][CH2:35][CH2:36][N:37]=5)[CH:28]=4)=[CH:16][CH:17]=3)[CH2:12]2)=[O:10])=[CH:4][C:3]=1[C:22]([F:23])([F:24])[F:25]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 962WaterHCID 10796Cesium carbonateHCID 58902317N-[4-chloro-3-(trifluoromethyl)phenyl]-7-hydroxy-1,2,3,4-tetrahydronaphthalene-2-carboxamideHCID 591349594-chloro-2-(4,5-dihydro-1H-imidazol-2-yl)pyridine

生成物 1

HCID 23585215N-[4-chloro-3-(trifluoromethyl)phenyl]-7-{[2-(4,5-dihydro-1H-imidazol-2-yl)-pyridin-4-yl]oxy}-1,2,3,4-tetrahydronaphthalene-2-carboxamide
収率 67.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of N-[4-chloro-3-(trifluoromethyl)phenyl]-7-hydroxy-1,2,3,4-tetrahydronaphthalene-2-carboxamide (64 mg, 0.17 mmol) and 4-chloro-2-(4,5-dihydro-1H-imidazol-2-yl)pyridine (35 mg, 0.19 mmol) in DMF (1.70 mL) was added Cs2CO3 (170 mg, 0.52 mmol). The mixture was irradiated in a microwave for 200 sec at 200° C. Water was added, and the mixture was extracted with EtOAc. The organic solution was washed with water (3×) and brine, dried over Na2SO4, filtered and evaporated. The residue was purified by column chromatography. The product was dissolved in MeOH, and 2.0M HCl in Et2O was added. The solvents were evaporated to give I-36 as a white solid (59 mg, 58%). 1H NMR (300 MHz, CD3OD): δ 8.62 (d, 1H), 8.17 (d, 1H), 7.82-7.78 (m, 1H), 7.63 (d, 1H), 7.53 (d, 1H), 7.25 (d, 1H), 7.21-7.18 (m, 1H), 6.96-6.91 (m, 2H), 4.11 (s, 4H), 3.14-2.82 (m, 5H), 2.24-2.16 (m, 1H), and 2.01-2.90 (m, 1H). LCMS: (FA) ES+ 516.2, ES− 513.2.

後処理

  1. customThe mixture was irradiated in a microwave for 200 sec at 200° C
  2. extractionthe mixture was extracted with EtOAc
  3. washThe organic solution was washed with water (3×) and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by column chromatography
  8. dissolutionThe product was dissolved in MeOH
  9. addition2.0M HCl in Et2O was added
  10. customThe solvents were evaporated

出典と根拠

ORDレコード
ord-9988032e1f5f40a898dd4443966accd6
出典データセット
uspto-grants-2012_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08110687B2

反応ノート

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