Triethylamine → HCID 44177732, compound

HRID 1890414Notes

Reaction equation

HRID 1890414 reaction equation
Br.[CH2:2]([O:4][C:5]([N:7]1[CH2:13][CH:12]([NH2:14])[C:11]2=[N:15][C:16]([C:20]3[CH:25]=[CH:24][N:23]=[CH:22][N:21]=3)=[CH:17][C:18](=[O:19])[N:10]2[CH2:9][CH2:8]1)=[O:6])[CH3:3].[Cl:26][C:27]1[CH:35]=[CH:34][C:30]([C:31](O)=[O:32])=[C:29]([O:36][CH3:37])[CH:28]=1.C(P(=O)(OCC)OCC)#N.C(N(CC)CC)C>CN(C)C=O>[CH2:2]([O:4][C:5]([N:7]1[CH2:13][CH:12]([NH:14][C:31](=[O:32])[C:30]2[CH:34]=[CH:35][C:27]([Cl:26])=[CH:28][C:29]=2[O:36][CH3:37])[C:11]2=[N:15][C:16]([C:20]3[CH:25]=[CH:24][N:23]=[CH:22][N:21]=3)=[CH:17][C:18](=[O:19])[N:10]2[CH2:9][CH2:8]1)=[O:6])[CH3:3]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 936824-Chloro-o-anisic acidHCID 68733660HCID 68733660, compound

Product 1

HCID 44177732HCID 44177732, compoundYield 53.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.060 g (0.18 mmol) of (+/−)-9-amino-4-oxo-2-pyrimidin-4-yl-5,6,8,9-tetrahydro-4H-1,4a,7-triaza-benzocycloheptene-7-carboxylic acid ethyl ester hydrobromide (1:1) dissolved in 1.80 mL of dimethylformamide was added 0.037 g (0.20 mmol) of 4-chloro-2-methoxy-benzoic acid. To the resulting mixture was added 40 μL (0.22 mmol) of diethyl cyanophosphonate and 30 μl (0.20 mmol) of triethylamine at 0° C. The resulting mixture was stirred at room temperature for 2 hours and evaporated to dryness. Water was added and the mixture extracted with dichloromethane. The extracts were washed with a saturated aqueous solution of sodium carbonate, saturated aqueous solution of ammonium chloride, saturated aqueous sodium chloride dried and evaporated. The residue was triturated with a mixture of diethyl ether/ethyl acetate and filtered to afford 0.048 g (53%) of the pure product as a powder.

Workup

  1. customevaporated to dryness
  2. additionWater was added
  3. extractionthe mixture extracted with dichloromethane
  4. washThe extracts were washed with a saturated aqueous solution of sodium carbonate, saturated aqueous solution of ammonium chloride, saturated aqueous sodium chloride
  5. customdried
  6. customevaporated
  7. customThe residue was triturated with a mixture of diethyl ether/ethyl acetate
  8. filtrationfiltered

Sources & evidence

ORD record
ord-c7aa8fb38dd1447e840ff27f3a92bd76
Source dataset
uspto-grants-2013_08
Patent number
US08507476B2

Reaction notes

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