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

HRID 44238Notes

Reaction equation

HRID 44238 reaction equation
[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

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31347SulfolaneSolvent

Conditions

Temperature
220 °C

Procedure

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.

Workup

  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.

Sources & evidence

ORD record
ord-32afe53ec2764c6c918dad79db1f0030
Source dataset
uspto-grants-2013_09
Patent number
US08541407B2

Reaction notes

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