Hydrochloric Acid → (s)-1-(2-Hydroxyethyl)-3-(5-chloroindole-2-carbonylamino)-3,4-dihydrocarbostyril

HRID 11582

반응식

HRID 11582 반응식
[C:1]([CH2:4][N:5]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9][C@H:8]([NH:16][C:17]([C:19]2[NH:20][C:21]3[C:26]([CH:27]=2)=[CH:25][C:24]([Cl:28])=[CH:23][CH:22]=3)=[O:18])[C:6]1=[O:7])(O)=[O:2].Cl.C(OCC)(=O)C>B.O1CCCC1>[OH:2][CH2:1][CH2:4][N:5]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9][C@H:8]([NH:16][C:17]([C:19]2[NH:20][C:21]3[C:26]([CH:27]=2)=[CH:25][C:24]([Cl:28])=[CH:23][CH:22]=3)=[O:18])[C:6]1=[O:7]

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 69195122(S)-1-carboxymethyl-3-(5-chloroindole-2-carbonylamino)-3,4-dihydrocarbostyril

생성물 1

HCID 69194918(s)-1-(2-Hydroxyethyl)-3-(5-chloroindole-2-carbonylamino)-3,4-dihydrocarbostyril수율 19%

시약·촉매·용매 2

HCID 6331Borane용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
35 °C

실험 절차

A mixture of (S)-1-carboxymethyl-3-(5-chloroindole-2-carbonylamino)-3,4-dihydrocarbostyril (Example 10) (6 mg) in 1.0 M borane in tetrahydrofuran solution (2 mL) under argon was stirred at 35° C. for 3 h. After cooling to room temperature, 1.0 M aqueous hydrochloric acid (10 mL) and ethyl acetate (10 mL) were added. This mixture was stirred for 3 h before the layers were separated. The organic phase was washed with water (10 mL three times) and evaporated under vacuum. The residue was chromatographed on reverse phase preparative HPLC to isolate the title compound (1.1 mg) and the over-reduction product (S)-1-(2-hydroxyethyl)-3-(5-chloroindole-2-carbonylamino)-1,2,3,4-tetrahydroquinoline (0.9 mg). Title compound HPLC/MS [M+H]+, 384.

후처리

  1. temperatureAfter cooling to room temperature
  2. stirringThis mixture was stirred for 3 h before the layers
  3. customwere separated
  4. washThe organic phase was washed with water (10 mL three times)
  5. customevaporated under vacuum
  6. customThe residue was chromatographed on reverse phase preparative HPLC

출처 및 근거

ORD 기록
ord-53c7f65f8f8a484284f4f588533f0f5f
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07098235B2

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