Hydrogen Bromide → (+/-)-Pyridine-2-carboxylic acid (4-oxo-2-pyrimidin-4-yl-4,5,6,7,8,9-hexahydro-1,4a,7-triaza-benzocyclohepten-9-yl)-amide

HRID 1890399Notes

Reaction equation

HRID 1890399 reaction equation
C(OC([N:6]1[CH2:12][CH:11]([NH:13][C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)=[O:15])[C:10]2=[N:22][C:23]([C:27]3[CH:32]=[CH:31][N:30]=[CH:29][N:28]=3)=[CH:24][C:25](=[O:26])[N:9]2[CH2:8][CH2:7]1)=O)C.Br>>[O:26]=[C:25]1[N:9]2[C:10]([CH:11]([NH:13][C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=3)=[O:15])[CH2:12][NH:6][CH2:7][CH2:8]2)=[N:22][C:23]([C:27]2[CH:32]=[CH:31][N:30]=[CH:29][N:28]=2)=[CH:24]1

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 44158890Ethyl 6,7,9,10-tetrahydro-4-oxo-10-[(2-pyridinylcarbonyl)amino]-2-(4-pyrimidinyl)pyrimido[1,2-d][1,4]diazepine-8(4H)-carboxylate

Product 1

HCID 44158892(+/-)-Pyridine-2-carboxylic acid (4-oxo-2-pyrimidin-4-yl-4,5,6,7,8,9-hexahydro-1,4a,7-triaza-benzocyclohepten-9-yl)-amideYield 56.7%

Conditions

Temperature
100 °C

Procedure

To a solution of 0.075 g (0.17 mmol) of (+/−)-4-oxo-9-[(pyridine-2-carbonyl)-amino]-2-pyrimidin-4-yl-5,6,8,9-tetrahydro-4H-1,4a,7-triaza-benzocycloheptene-7-carboxylic acid ethyl ester (example 1) dissolved in 0.6 mL (3.44 mmol) of hydrobromic acid (33 wt % solution in glacial acetic acid). The resulting mixture was stirred at 100° C. for 8 hours, cooled and evaporated to dryness. Toluene was added to the residue and evaporated. MeOH added to the residue and evaporated. After an acido-basic work-up, the crude was triturated with diethyl ether and filtered to afford 0.035 g (45%) of the product as a white powder and free base.

Workup

  1. temperaturecooled
  2. customevaporated to dryness
  3. additionToluene was added to the residue
  4. customevaporated
  5. additionMeOH added to the residue
  6. customevaporated
  7. customAfter an acido-basic work-up, the crude was triturated with diethyl ether
  8. filtrationfiltered

Sources & evidence

ORD record
ord-10f5b9c98a214064884670aa3fd7336f
Source dataset
uspto-grants-2013_08
Patent number
US08507475B2

Reaction notes

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