Resorcinol → 2-chloro-5,11-dihydro-11-ethyl-8-(3-hydroxyphenyl)methyl-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one

HRID 724976노트

반응식

HRID 724976 반응식
[C:1]1([CH:8]=[CH:7][CH:6]=[C:4]([OH:5])[CH:3]=1)O.CC(C)([O-])C.[K+].[Cl:15][C:16]1[CH:17]=[CH:18][C:19]2[N:20]([CH3:36])[C:21](=[O:35])[C:22]3[CH:32]=[C:31]([CH2:33]Cl)[CH:30]=[N:29][C:23]=3[N:24]([CH2:27][CH3:28])[C:25]=2[N:26]=1>CS(C)=O.C(OCC)(=O)C>[Cl:15][C:16]1[CH:17]=[CH:18][C:19]2[N:20]([CH3:36])[C:21](=[O:35])[C:22]3[CH:32]=[C:31]([CH2:33][C:1]4[CH:8]=[CH:7][CH:6]=[C:4]([OH:5])[CH:3]=4)[CH:30]=[N:29][C:23]=3[N:24]([CH2:27][CH3:28])[C:25]=2[N:26]=1

참가 물질

6

반응물 3

HCID 5054ResorcinolHCID 108307382-chloro-8-chloromethyl-5,11-dihydro-11-ethyl-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-oneHCID 23665647Potassium tert-butoxide

생성물 1

HCID 159563382-chloro-5,11-dihydro-11-ethyl-8-(3-hydroxyphenyl)methyl-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one수율 56.1%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매2회HCID 8857Ethyl Acetate용매

실험 절차

Resorcinol (0.082 g, 0.74 mmol) in dimethyl sulfoxide (1 mL) was treated with potassium tert-butoxide (1.0M in tetrahydrofuran, 0.15 mL, 0.15 mmol). The resulting stirred solution was treated with 2-chloro-8-chloromethyl-5,11-dihydro-11-ethyl-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one (0.050 g, 0.14 mmol) in dimethyl sulfoxide (1 mL) and the mixture was stirred an additional 16 hours. The mixture was diluted with ethyl acetate (50 mL) washed with brine, water, and brine (15 mL each). The organics were dried over sodium sulfate, concentrated and the residue was purified by flash chromatography (hexanes to 1:1 hexanes/ethyl acetate gradient) followed by crystallization from hexanes to give the title compound (0.031 g, 51%), m.p. 219°-220° C.

후처리

  1. stirringthe mixture was stirred an additional 16 hours
  2. washwashed with brine, water, and brine (15 mL each)
  3. dry with materialThe organics were dried over sodium sulfate
  4. concentrationconcentrated
  5. customthe residue was purified by flash chromatography (hexanes to 1:1 hexanes/ethyl acetate gradient)
  6. customfollowed by crystallization from hexanes

출처 및 근거

ORD 기록
ord-7cd25f6d86a145dc94cc7ac0bae4962f
출처 데이터셋
uspto-grants-1998_01
특허 번호
US05705499

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