Hydrochloric Acid → (S)-3-(5-chloroindole-2-carbonylamino)-1-cyanomethyl-3,4-dihydrocarbostyril

HRID 1828350

反応式

HRID 1828350 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([NH:13][C@H:14]1[CH2:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[NH:16][C:15]1=[O:24])=[O:12])=[CH:5]2.C[O-].[Na+].Br[CH2:29][C:30]#[N:31].Cl>O1CCCC1.C(OCC)(=O)C.O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([NH:13][C@H:14]1[CH2:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]([CH2:29][C:30]#[N:31])[C:15]1=[O:24])=[O:12])=[CH:5]2

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 11534BromoacetonitrileHCID 10942334Sodium MethoxideHCID 44357926(S)-3-(5-chloroindole-2-carbonylamino)-3,4-dihydrocarbostyril

生成物 1

HCID 87730389(S)-3-(5-chloroindole-2-carbonylamino)-1-cyanomethyl-3,4-dihydrocarbostyril収率 26.8%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

(S)-3-(5-chloroindole-2-carbonylamino)-3,4-dihydrocarbostyril (Example 4, 13.4 mg) was dissolved in tetrahydrofuran (5 mL) at room temperature under argon with stirring. After cooing to 0° C., sodium methoxide (4.3 mg) was added, followed 2 h later by bromoacetonitrile (7.2 mg). This was warmed to room temperature over 2 h, and 2 h later water (15 mL), 1.0 M aqueous hydrochloric acid (1 mL), and ethyl acetate (20 mL) were added. The organic phase was separated, washed with brine, and dried over anhydrous sodium sulfate. After solvent evaporation under vacuum, the crude product was purified by reverse phase preparative HPLC to provide the title compound (4 mg). HPLC/MS [M+H]+, 379; HPLC/MS [M+Na]+, 401.

後処理

  1. customAfter cooing to 0° C.
  2. customThe organic phase was separated
  3. washwashed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customAfter solvent evaporation under vacuum
  6. customthe crude product was purified by reverse phase preparative HPLC

出典と根拠

ORDレコード
ord-b3ef261f456e4b509481a2dfba22d5f9
出典データセット
uspto-grants-2006_06
特許番号
US07057046B2

関連ノート

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