Ethyl Acetate → 1-cyclohexyl-4H,6H-2,3,6,10b-tetraaza-benzo[e]azulen-5-one

HRID 900126

반응식

HRID 900126 반응식
C(O[C:4]1[CH2:10][C:9](=[O:11])[NH:8][C:7]2[CH:12]=[CH:13][CH:14]=[CH:15][C:6]=2[N:5]=1)C.[CH:16]1([C:22]([NH:24][NH2:25])=O)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1.CCOC(C)=O.C([O-])(O)=O.[Na+]>C(O)(=O)C.CCOCC.O>[CH:16]1([C:22]2[N:5]3[C:4]([CH2:10][C:9](=[O:11])[NH:8][C:7]4[CH:12]=[CH:13][CH:14]=[CH:15][C:6]=43)=[N:25][N:24]=2)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1

참가 물질

8

반응물 4

HCID 8857Ethyl AcetateHCID 240039CyclohexanecarbohydrazideHCID 516892Sodium BicarbonateHCID 589579152H-1,5-Benzodiazepin-2-one, 4-ethoxy-1,3-dihydro-

생성물 1

HCID 589579321-cyclohexyl-4H,6H-2,3,6,10b-tetraaza-benzo[e]azulen-5-one

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 962Water용매HCID 3283Diethyl Ether용매

반응 조건

온도
120 °C

실험 절차

To a solution of 4-ethoxy-1,3-dihydro-benzo[b][1,4]diazepin-2-one (Preparation 3(A) (5 g, 24.5 mmol) in glacial acetic acid (75 mL) was added cyclohexanecarboxylic acid hydrazide (Preparation 14) (3.5 g, 24.5 mmol). The reaction was heated at 120° C. for 2.5 hours, was cooled to room temperature, and EtOAc (50 mL), water (50 mL) and aqueous NaHCO3 (50 mL) were added. The mixture was stirred for 5 minutes and Et2O was added (125 mL). The suspension was stirred for 15 minutes and the solids were removed by filtration with the aid of Et2O to provide 5.92 g of 1-cyclohexyl-4H,6H-2,3,6,10b-tetraaza-benzo[e]azulen-5-one. 1H NMR (CDCl3) δ 8.36 (s, NH), 7.50 (m, 1H), 7.41 (m, 2H), 7.30 (d, 1H), 4.13 (d, 1H), 3.47 (d, 1H), 2.87 (m, 1H), 2.24 (d, 1H), 2.00 (m, 2H), 1.72-1.51 (m, 4H), 1.33 (m, 2H), 1.16 (m, 1H); MS 283.4 (M+1), 281.3 (M−1).

후처리

  1. temperaturewas cooled to room temperature
  2. stirringThe suspension was stirred for 15 minutes
  3. customthe solids were removed by filtration with the aid of Et2O

출처 및 근거

ORD 기록
ord-681642658a624ab3927ac4f4c3b58618
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07358242B2

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