2H-Azepine, 3,4,5,6-tetrahydro-7-methoxy- → 3-bromo-7,8,9,10-tetrahydropyrido[3',2':4,5]pyrimido[1,2-a]azepin-12(6H)-one

HRID 1619376Notes

Reaction equation

HRID 1619376 reaction equation
CO[C:3]1[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][N:9]=1.[NH2:10][C:11]1[C:12]([C:18](O)=[O:19])=[N:13][CH:14]=[C:15]([Br:17])[CH:16]=1>CN(C=O)C.O>[Br:17][C:15]1[CH:14]=[N:13][C:12]2[C:18](=[O:19])[N:9]3[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][C:3]3=[N:10][C:11]=2[CH:16]=1

Participants

5

Reactant 2

HCID 756572H-Azepine, 3,4,5,6-tetrahydro-7-methoxy-HCID 497615813-Amino-5-bromopyridine-2-carboxylic acid

Product 1

HCID 585742973-bromo-7,8,9,10-tetrahydropyrido[3',2':4,5]pyrimido[1,2-a]azepin-12(6H)-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 7-methoxy-3,4,5,6-tetrahydro-2H-azepine (1.0 g, 8.8 mmol) and 3-amino-5-bromopicolinic acid (1.9 g, 8.8 mmol) in DMF (70 mL) was stirred at 130° C. for 48 h. The reaction mixture was diluted with H2O (300 mL) and extracted with DCM (3×300 mL). The combined organic layers were washed with saturated sodium carbonate and brine, dried over Na2SO4. After filtration and concentration, the residue was purified by silica gel chromatography to give the desired product. MS (ESI):294, 296 (MH+).

Workup

  1. extractionextracted with DCM (3×300 mL)
  2. washThe combined organic layers were washed with saturated sodium carbonate and brine
  3. dry with materialdried over Na2SO4
  4. filtrationAfter filtration and concentration
  5. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-8bcb5c8ae93f4cc6b702e5d4df988097
Source dataset
uspto-grants-2014_07
Patent number
US08772301B2

Reaction notes

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