Triethylamine → (+/-)-4-Chloro-2-methoxy-N-(4-oxo-2-pyrimidin-4-yl-5,6,8,9-tetrahydro-4H-7-oxa-1,4a-diaza-benzocyclohepten-9-yl)benzamide

HRID 1890240Notes

Reaction equation

HRID 1890240 reaction equation
[NH2:1][CH:2]1[C:8]2=[N:9][C:10]([C:14]3[CH:19]=[CH:18][N:17]=[CH:16][N:15]=3)=[CH:11][C:12](=[O:13])[N:7]2[CH2:6][CH2:5][O:4][CH2:3]1.[Cl:20][C:21]1[CH:29]=[CH:28][C:24]([C:25](O)=[O:26])=[C:23]([O:30][CH3:31])[CH:22]=1.C(P(=O)(OCC)OCC)#N.C(N(CC)CC)C>CN(C)C=O.C(OCC)(=O)C.O>[Cl:20][C:21]1[CH:29]=[CH:28][C:24]([C:25]([NH:1][CH:2]2[C:8]3=[N:9][C:10]([C:14]4[CH:19]=[CH:18][N:17]=[CH:16][N:15]=4)=[CH:11][C:12](=[O:13])[N:7]3[CH2:6][CH2:5][O:4][CH2:3]2)=[O:26])=[C:23]([O:30][CH3:31])[CH:22]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 936824-Chloro-o-anisic acidHCID 68626960HCID 68626960, compound

Product 1

HCID 44159260(+/-)-4-Chloro-2-methoxy-N-(4-oxo-2-pyrimidin-4-yl-5,6,8,9-tetrahydro-4H-7-oxa-1,4a-diaza-benzocyclohepten-9-yl)benzamideYield 81%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 0.700 g (2.70 mmol) of (+/−)-9-amino-2-pyrimidin-4-yl-5,6,8,9-tetrahydro-7-oxa-1,4a-diaza-benzocyclohepten-4-one dissolved in 54 mL of dimethylformamide was added 0.554 g (2.97 mmol) of 4-chloro-2-methoxy-benzoic acid. To the resulting mixture was added 440 μL (2.97 mmol) of diethyl cyanophosphonate and 450 μL (3.24 mmol) of triethylamine at 0° C. The resulting mixture was stirred at room temperature for 4 hours. Water and ethyl acetate were added and the mixture was stirred. The resulting residue was filtered, washed with water, ethyl acetate and diethyl ether to afford 0.932 g (81%) of the pure product as a white powder.

Workup

  1. stirringthe mixture was stirred
  2. filtrationThe resulting residue was filtered
  3. washwashed with water, ethyl acetate and diethyl ether

Sources & evidence

ORD record
ord-d6c4db61234b4c5e8b92544cd9e03def
Source dataset
uspto-grants-2013_08
Patent number
US08507470B2

Reaction notes

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