Pentafluorophenol → HCID 135506890, compound

HRID 1289232Notes

Reaction equation

HRID 1289232 reaction equation
[CH3:1][C:2]1[NH:11][C:10](=[O:12])[C:9]2[C:4](=[CH:5][C:6]3[CH2:15][CH2:14][C@H:13]([N:16]([C:20]4[CH:28]=[CH:27][C:23]([C:24]([OH:26])=[O:25])=[CH:22][CH:21]=4)[CH2:17][C:18]#[CH:19])[C:7]=3[CH:8]=2)[N:3]=1.[F:29][C:30]1[C:35](O)=[C:34]([F:37])[C:33]([F:38])=[C:32]([F:39])[C:31]=1[F:40]>CC(N(C)C)=O>[CH3:1][C:2]1[NH:11][C:10](=[O:12])[C:9]2[C:4](=[CH:5][C:6]3[CH2:15][CH2:14][C@H:13]([N:16]([C:20]4[CH:21]=[CH:22][C:23]([C:24]([O:26][C:35]5[C:34]([F:37])=[C:33]([F:38])[C:32]([F:39])=[C:31]([F:40])[C:30]=5[F:29])=[O:25])=[CH:27][CH:28]=4)[CH2:17][C:18]#[CH:19])[C:7]=3[CH:8]=2)[N:3]=1

Participants

4

Reactant 2

HCID 13041PentafluorophenolHCID 135529903HCID 135529903, compound

Product 1

HCID 135506890HCID 135506890, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent2×

Procedure

A solution of p-[N-((6S)-2-methyl-4-oxo-3,4,7,8-tetrahydro-6H-cyclopenta-[g]quinazolin-6-yl)-N-(prop-2-ynyl)amino]benzoic acid (0.7 g) in DMA (25 ml) was added to a stirred mixture of pentafluorophenol (1.2 g), N,N-dicyclohexylcarbodiimide (0.45 g) and DMA (50 ml). The resultant mixture was stirred at 50° C. for 18 hours. The mixture was evaporated and the residue was purified by column chromatography using initially a 40:1 and then a 20:1 mixture of methylene chloride and methanol as eluant. There was thus obtained pentafluorophenyl p-[N-((6S)-2-methyl-4-oxo-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl)-N-(prop-2-ynyl)-amino]benzoate as a solid (0.57 g);

Workup

  1. customThe mixture was evaporated
  2. customthe residue was purified by column chromatography
  3. additiona 20:1 mixture of methylene chloride and methanol as eluant

Sources & evidence

ORD record
ord-2fa2d013bb3b49908d58b932d90efd91
Source dataset
uspto-grants-1998_05
Patent number
US05747499

Reaction notes

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