Trifluoroacetic acid → HCID 135848306, compound

HRID 1289236Notes

Reaction equation

HRID 1289236 reaction equation
[CH3:1][N:2]([C:18]1[CH:19]=[CH:20][C:21]([C:24]([OH:26])=[O:25])=[N:22][CH:23]=1)[CH:3]1[C:7]2[CH:8]=[C:9]3[C:14](=[CH:15][C:6]=2[CH2:5][CH2:4]1)[N:13]=[C:12]([CH3:16])[NH:11][C:10]3=[O:17].FC(F)(F)C(O[C:32]1[C:37]([F:38])=[C:36]([F:39])[C:35]([F:40])=[C:34]([F:41])[C:33]=1[F:42])=O.FC1C(O)=C(F)C(F)=C(F)C=1F.FC(F)(F)C(O)=O>CC(N(C)C)=O.N1C=CC=CC=1>[CH3:1][N:2]([C:18]1[CH:19]=[CH:20][C:21]([C:24]([O:26][C:32]2[C:33]([F:42])=[C:34]([F:41])[C:35]([F:40])=[C:36]([F:39])[C:37]=2[F:38])=[O:25])=[N:22][CH:23]=1)[CH:3]1[C:7]2[CH:8]=[C:9]3[C:14](=[CH:15][C:6]=2[CH2:5][CH2:4]1)[N:13]=[C:12]([CH3:16])[NH:11][C:10]3=[O:17]

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 13041PentafluorophenolHCID 4327891Pentafluorophenyl TrifluoroacetateHCID 135966603HCID 135966603, compound

Product 1

HCID 135848306HCID 135848306, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 31374DimethylacetamideSolvent

Procedure

A mixture of 5-[N-methyl-N-((6RS)-2-methyl-4-oxo-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl)amino]pyridine-2-carboxylic acid (0.01 g), pentafluorophenyl trifluoroacetate (0.16 g; prepared by the reaction of pentafluorophenol and trifluoroacetic acid), pyridine (0.045 g) and DMA (5 ml) was stirred at ambient temperature for 5 hours. The mixture was evaporated and the residue was partitioned between ethyl acetate and a saturated aqueous sodium bicarbonate solution. The organic phase was dried (MgSO4) and evaporated. The residue was purified by column chromatography using increasingly polar mixtures of ethyl acetate and methanol as eluant. There was thus obtained pentafluorophenyl 5-[N-methyl-N-((6RS)-2-methyl-4-oxo-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl)amino]-pyridine-2-carboxylate as a foam (0.1 g);

Workup

  1. customThe mixture was evaporated
  2. customthe residue was partitioned between ethyl acetate
  3. dry with materialThe organic phase was dried (MgSO4)
  4. customevaporated
  5. customThe residue was purified by column chromatography
  6. temperatureusing increasingly polar mixtures of ethyl acetate and methanol as eluant

Sources & evidence

ORD record
ord-095be6ce2cdf4b5fb8a493ddb8ef0016
Source dataset
uspto-grants-1998_05
Patent number
US05747499

Reaction notes

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