Dimethyl acetylenedicarboxylate → 1-carbomethoxy-9-chloro-7-phenylpyrimido[1,2-a][1,4]benzodiazepin-3(5H)-one

HRID 1111214

반응식

HRID 1111214 반응식
[NH2:1][C:2]1[CH2:8][N:7]=[C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:5]2[CH:15]=[C:16]([Cl:19])[CH:17]=[CH:18][C:4]=2[N:3]=1.[C:20]([C:26](OC)=[O:27])#[C:21][C:22]([O:24][CH3:25])=[O:23]>CO>[C:22]([C:21]1[N:3]2[C:4]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:5]=3[C:6]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)=[N:7][CH2:8][C:2]2=[N:1][C:26](=[O:27])[CH:20]=1)([O:24][CH3:25])=[O:23]

참가 물질

4

반응물 2

HCID 12980Dimethyl acetylenedicarboxylateHCID 165626N-Desmethyl-N(4)-desoxychlordiazepoxide

생성물 1

HCID 150797811-carbomethoxy-9-chloro-7-phenylpyrimido[1,2-a][1,4]benzodiazepin-3(5H)-one수율 16.3%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A mixture of 2-amino-7-chloro-5-phenyl-3H-1,4-benzodiazepine (13.5 g.; 0.05 mole), dimethyl acetylenedicarboxylate (7.1 g.; 0.05 mole) and 250 ml. of methanol were refluxed for 2 hours and evaporated. The residue was dissolved in 50 ml. of methylene chloride and chromatographed on 2 kg. of silica gel using 60% ethyl acetate 40% cyclohexane. Fractions 1-6 (4.5 l.) gave no material. Fractions 6-51 were discarded. Fraction 52-54 gave 6.3 g. of solids which were crystallized from methylene chloride ether to give 1-carbomethoxy-9-chloro-7-phenylpyrimido[1,2-a][1,4]benzodiazepin-3(5H)-one 3.1 g. of melting point 214°-215° C. dec., raised to 216°-217° C. on recrystallization from methanol-ether.

후처리

  1. customevaporated
  2. dissolutionThe residue was dissolved in 50 ml
  3. customof methylene chloride and chromatographed on 2 kg
  4. customFractions 1-6 (4.5 l.) gave no material
  5. customFraction 52-54 gave 6.3 g
  6. customof solids which were crystallized from methylene chloride ether

출처 및 근거

ORD 기록
ord-a98ebb1abd7442d2b69b0d826b53ddd1
출처 데이터셋
uspto-grants-1990_12
특허 번호
US04978753

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