Hydrochloric Acid → Efipladib

HRID 854710

반응식

HRID 854710 반응식
[CH:1]([N:14]1[C:22]2[C:17](=[CH:18][C:19]([Cl:23])=[CH:20][CH:21]=2)[C:16]([CH2:24][CH2:25][CH2:26][C:27]2[CH:37]=[CH:36][C:30]([C:31]([O:33]CC)=[O:32])=[CH:29][CH:28]=2)=[C:15]1[CH2:38][CH2:39][NH:40][S:41]([CH2:44][C:45]1[CH:50]=[CH:49][C:48]([Cl:51])=[C:47]([Cl:52])[CH:46]=1)(=[O:43])=[O:42])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li+].[OH-].CO.Cl>O.C1COCC1>[Cl:23][C:19]1[CH:18]=[C:17]2[C:22](=[CH:21][CH:20]=1)[N:14]([CH:1]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:15]([CH2:38][CH2:39][NH:40][S:41]([CH2:44][C:45]1[CH:50]=[CH:49][C:48]([Cl:51])=[C:47]([Cl:52])[CH:46]=1)(=[O:43])=[O:42])=[C:16]2[CH2:24][CH2:25][CH2:26][C:27]1[CH:28]=[CH:29][C:30]([C:31]([OH:33])=[O:32])=[CH:36][CH:37]=1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 3939Lithium HydroxideHCID 11239705Ethyl 4-{3-[1-benzhydryl-5-chloro-2-(2-{[(3,4-dichlorobenzyl)sulfonyl]amino}ethyl)-1H-indol-3-yl]propyl}benzoate

생성물 1

HCID 9853499Efipladib수율 96%

시약·촉매·용매 2

HCID 962Water용매2회HCID 8028Tetrahydrofuran용매

실험 절차

A solution of ethyl 4-{3-[1-benzhydryl-5-chloro-2-(2-{[(3,4-dichlorobenzyl)sulfonyl]-amino}ethyl)-1H-indol-3-yl]propyl}benzoate (0.50 g, 0.65 mmol), LiOH (0.24 g, 10.0 mmol), methanol (5 mL), THF (5 mL) and water (5 mL) was stirred for 18 h at rt, then diluted with water (200 mL). 1 N HCl (10 mL) was added. The reaction mixture was extracted with EtOAc (2×50 mL). The organic extracts were dried over Na2SO4. The solvent is evaporated to give a white solid (0.46 g, 96%). 1H NMR (DMSO-d6): δ12.80 (br.s, 1H), 7.89 (d, 2H, J=2 Hz), 7.59 (d, 1H, J=1.5 Hz), 7.53 (d, 1H, J=6 Hz), 7.48 (d, 1H, J=1.5 Hz), 7.38 (m, 9H), 7.20 (m, 5H), 6.77 (dd, 1H, J=6.9 & 1.5 Hz), 6.46 (d, 1H, J=6.9 Hz), 4.36 (s, 2H), 3.18 (m,2H), 2.96 (m,2H), 2.76 (m, 4H), 1.90(m, 2H).

후처리

  1. extractionThe reaction mixture was extracted with EtOAc (2×50 mL)
  2. dry with materialThe organic extracts were dried over Na2SO4
  3. customThe solvent is evaporated

출처 및 근거

ORD 기록
ord-aed37f2423b94b30b3410ac9578f5e54
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07259277B2

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