Citric Acid → HCID 18962909, compound

HRID 373853Notes

Reaction equation

HRID 373853 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:26][N:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)[C:5]2[O:14][CH2:13][C:12]3[C:11]([C:15](=[O:19])[CH2:16][C:17]#[N:18])=[N:10][N:9]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[C:8]=3[C:6]=2[CH:7]=1.[C:33]1([N:39]=[C:40]=[O:41])[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.C(N(CC)CC)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C)C=O>[C:17]([CH:16]([C:15]([C:11]1[C:12]2[CH2:13][O:14][C:5]3[C:4]([CH2:26][N:27]4[CH2:28][CH2:29][O:30][CH2:31][CH2:32]4)=[CH:3][C:2]([F:1])=[CH:7][C:6]=3[C:8]=2[N:9]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:10]=1)=[O:19])[C:40]([NH:39][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:41])#[N:18]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 7672Phenyl isocyanateHCID 8471TriethylamineHCID 19808379HCID 19808379, compound

Product 1

HCID 18962909HCID 18962909, compoundYield 53.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-(8-fluoro-1,4-dihydro-6-morpholinomethyl-1-phenyl-[1]-benzopyrano[4,3-c]pyrazol-3-yl)-3-oxo-propanenitrile (2.8 g) is reacted with phenylisocyanate (0.8 g) in dimethylformamide (20 ml) in the presence of triethylamine (0.7 g) at 25°-30° C. for 30 min. The reaction mixture is diluted with ice water and acidified with citric acid to pH 3. The precipitate is filtered and dissolved in chloroform. The organic solution is washed with 2% citric acid solution and then with water until neutral. Evaporation to dryness in vacuo gives a residue which is crystallized from chloroform/ethanol to yield 1.9 g of 2-cyano-3-(8-fluoro-1,4-dihydro-6-morpholinomethyl-1-phenyl-[1]-benzopyrano[4,3-c]pyrazol-3-yl)-3-oxo-N-phenyl-propanamide, m.p. 249°-253° C.

Workup

  1. filtrationThe precipitate is filtered
  2. dissolutiondissolved in chloroform
  3. washThe organic solution is washed with 2% citric acid solution
  4. customEvaporation to dryness in vacuo
  5. customgives a residue which
  6. customis crystallized from chloroform/ethanol

Sources & evidence

ORD record
ord-d6b716c864614a898de27526f7e7de69
Source dataset
uspto-grants-1992_11
Patent number
US05166152

Reaction notes

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