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Hydrochloric Acid → 13-Cyclohexyl-6,7-dihydro-6-oxo-5H-indolo[2,1-a][2]benzazepine-10-carboxylic acid

HRID 1394879
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HRID 1394879 반응식
[OH-].[Na+].[CH:3]1([C:9]2[C:10]3[CH:11]=[CH:12][C:13]([C:28]([O:30]C)=[O:29])=[CH:14][C:15]=3[N:16]3[CH2:22][C:21](=[O:23])[CH2:20][C:19]4[CH:24]=[CH:25][CH:26]=[CH:27][C:18]=4[C:17]=23)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.Cl>CO.O1CCCC1>[CH:3]1([C:9]2[C:10]3[CH:11]=[CH:12][C:13]([C:28]([OH:30])=[O:29])=[CH:14][C:15]=3[N:16]3[CH2:22][C:21](=[O:23])[CH2:20][C:19]4[CH:24]=[CH:25][CH:26]=[CH:27][C:18]=4[C:17]=23)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]1
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참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58765241methyl 13-cyclohexyl-6,7-dihydro-6-oxo-5H-indolo[2,1-a][2]benzazepine-10-carboxylate

생성물 1

HCID 5876518713-Cyclohexyl-6,7-dihydro-6-oxo-5H-indolo[2,1-a][2]benzazepine-10-carboxylic acid수율 92.7%

시약·촉매·용매 2

HCID 887Methanol용매
HCID 8028
Tetrahydrofuran
용매

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온도
90 °C

실험 절차

Sodium hydroxide (0.2 mL of 1 N, 0.2 mmol) was added to a solution of the Methyl 13-cyclohexyl-6,7-dihydro-6-oxo-5H-indolo[2,1-a][2]benzazepine-10-carboxylate (20 mg, 0.052 mmol) in methanol (0.5 mL) and tetrahydrofuran (0.5 mL) in a microwave vial. The vial was sealed and the contents heated at 90° C. for 5 min in a microwave apparatus. The solution was acidified with dilute hydrochloric acid to precipitate the crude acid. The solid was collected and purified on the Shimadzu preparative liquid chromatograph. The product containing fraction was concentrated on a Speed Vac® to leave the titled compound as a white solid (18 mg, 92%). ESI-MS m/z 374 (MH+); 1H NMR (500 MHz, ACETONE-D6) δ 1.22-1.35 (m, 1 H) 1.41-1.58 (m, 2 H) 1.59-1.70 (m, 1 H) 1.73-1.85 (m, 2 H) 1.92-2.00 (m, 1 H) 2.11-2.26 (m, 3 H) 3.04 (m, 1 H) 3.60 (d, J=14.04 Hz, 1 H) 3.97 (d, J=13.73 Hz, 1 H) 4.56 (d, J=18.31 Hz, 1 H) 5.19 (d, J=18.31 Hz, 1 H) 7.51 (m, 2 H) 7.57 (t, J=7.32 Hz, 1 H) 7.66 (d, J=7.63 Hz, 1 H) 7.81 (dd, J=8.39, 1.37 Hz, 1 H) 8.03 (d, J=8.24 Hz, 1H 8.23 (s, 3 H).

후처리

  1. customThe vial was sealed
  2. customto precipitate the crude acid
  3. customThe solid was collected
  4. custompurified on the Shimadzu preparative liquid chromatograph
  5. additionThe product containing fraction
  6. concentrationwas concentrated on a Speed Vac®

출처 및 근거

ORD 기록
ord-48fd24608ede433a81abcb1de5a45046
출처 데이터셋
uspto-grants-2008_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07348425B2

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