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 724976ノート

反応式

HRID 724976 の反応式
[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

参加物

6

反応物 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

生成物 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-one収率 56.1%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-7cd25f6d86a145dc94cc7ac0bae4962f
出典データセット
uspto-grants-1998_01
特許番号
US05705499

反応ノート

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