Hydrochloric Acid → 8-methyl-5H-benzo[e]pyrido[3,2-b][1,4]diazepin-6(11H)-one

HRID 44238노트

반응식

HRID 44238 반응식
[NH2:1][C:2]1[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][C:3]=1[C:4]([NH:6][C:7]1[C:8](Cl)=[N:9][CH:10]=[CH:11][CH:12]=1)=[O:5].Cl>S1(CCCC1)(=O)=O.C(OCC)(=O)C>[CH3:18][C:15]1[CH:16]=[CH:17][C:2]2[NH:1][C:8]3[N:9]=[CH:10][CH:11]=[CH:12][C:7]=3[NH:6][C:4](=[O:5])[C:3]=2[CH:14]=1

참가 물질

5

반응물 2

HCID 313Hydrochloric AcidHCID 140754362-amino-N-(2-chloropyridin-3-yl)-5-methylbenzamide

생성물 1

HCID 129429478-methyl-5H-benzo[e]pyrido[3,2-b][1,4]diazepin-6(11H)-one수율 70.2%

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 31347Sulfolane용매

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온도
220 °C

실험 절차

A solution of 2-amino-N-(2-chloropyridin-3-yl)-5-methylbenzamide (2.515 g, 9.61 mmol) in sulfolane (15 mL) was treated with hydrogen chloride (0.25 mL, 1.0 mmol; 4N in dioxane). The reaction mixture was heated to 220° C. under microwave conditions for 8 minutes. The reaction mixture was then diluted with ethyl acetate (75 mL) and washed with water (5×50 mL). The organic layer (aqueous emulsion) was concentrated to give an aqueous slurry which was filtered and washed with water (50 mL). The product was dried under high vacuum at 60° C. to afford 8-methyl-5H-benzo[e]pyrido[3,2-b][1,4]diazepin-6(11H)-one (1.52 g) that was used without further purification. LCMS [M+H]: 226.

후처리

  1. washwashed with water (5×50 mL)
  2. concentrationThe organic layer (aqueous emulsion) was concentrated
  3. customto give an aqueous slurry which
  4. filtrationwas filtered
  5. washwashed with water (50 mL)
  6. customThe product was dried under high vacuum at 60° C.

출처 및 근거

ORD 기록
ord-32afe53ec2764c6c918dad79db1f0030
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541407B2

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