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Ammonium Chloride → (R)-1-(1-acryloylpiperidin-3-yl)-2-(3-(trifluoromethyl)benzamido)-1H-benzo[d]imidazole-5-carboxamide

HRID 60078
ノート
印刷プレビュー

反応式

HRID 60078 の反応式
[C:1]([N:5]1[CH2:10][CH2:9][CH2:8][C@@H:7]([N:11]2[C:15]3[CH:16]=[CH:17][C:18]([C:20](O)=[O:21])=[CH:19][C:14]=3[N:13]=[C:12]2[NH:23][C:24](=[O:35])[C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([F:34])([F:33])[F:32])[CH:26]=2)[CH2:6]1)(=[O:4])[CH:2]=[CH2:3].[NH4+].[Cl-].OC1C2N=N[NH:44]C=2C=CC=1.Cl.C(N=C=NCCCN(C)C)C>CN(C=O)C.O>[C:1]([N:5]1[CH2:10][CH2:9][CH2:8][C@@H:7]([N:11]2[C:15]3[CH:16]=[CH:17][C:18]([C:20]([NH2:44])=[O:21])=[CH:19][C:14]=3[N:13]=[C:12]2[NH:23][C:24](=[O:35])[C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([F:32])([F:34])[F:33])[CH:26]=2)[CH2:6]1)(=[O:4])[CH:2]=[CH2:3]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 25517Ammonium ChlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 72704604(R)-1-(1-acryloylpiperidin-3-yl)-2-(3-(trifluoromethyl)benzamido)-1H-benzo[d]imidazole-5-carboxylic acidHCID 178418300HCID 178418300、化合物

生成物 1

HCID 72704606(R)-1-(1-acryloylpiperidin-3-yl)-2-(3-(trifluoromethyl)benzamido)-1H-benzo[d]imidazole-5-carboxamide

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a solution of Example 18 (50 mg, 0.1 mmol) and NH4Cl (7 mg, 0.11 mmol) in DMF (4 mL) were added hydroxybenzotriazole (15 mg, 0.11 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (21 mg, 0.11 mmol) and the mixture was stirred at room temperature for 14 h (completion of reaction monitored by TLC). The mixture was diluted with water and extracted with CH2Cl2 (3×20 mL). The combined organic phase was washed with water and brine, dried over Na2SO4 and concentrated under reduced pressure. The crude material was purified by column chromatography (10% MeOH in CH2Cl2) to afford the title compound (Example 19). 1H-NMR (400 MHz, DMSO-d6): ∂ 13.0 (br s, 1H), 8.47 (d, J=7.2 Hz, 2H), 8.06-7.73 (m, 6H), 7.35 (s, 1H), 6.92-6.79 (m, 1H), 6.17-6.13 (m, 1H), 5.75-5.60 (m, 1H), 4.81-4.60 (m, 2H), 4.29-4.10 (m, 1H), 2.84-2.72 (m, 1H), 2.17-1.94 (m, 3H), 1.65 (s, 2H); MS calculated for C24H23F3N5O3 (M+H+) 486.17. found 486.3.

後処理

  1. custom(completion of reaction monitored by TLC)
  2. extractionextracted with CH2Cl2 (3×20 mL)
  3. washThe combined organic phase was washed with water and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe crude material was purified by column chromatography (10% MeOH in CH2Cl2)

出典と根拠

ORDレコード
ord-f6e88cbe65874830a2c42c189bab890c
出典データセット
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09440957B2

反応ノート

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