HCID 19066354, compound → HCID 19066330, compound

HRID 1289233Notes

Reaction equation

HRID 1289233 reaction equation
C(OC([N:8]([C:32]1[CH:33]=[CH:34][C:35]([C:38]([O:40][CH3:41])=[O:39])=[N:36][CH:37]=1)[CH:9]1[C:13]2[CH:14]=[C:15]3[C:20](=[CH:21][C:12]=2[CH2:11][CH2:10]1)[N:19]=[C:18]([CH3:22])[N:17]([CH2:23][O:24][C:25](=[O:30])[C:26]([CH3:29])([CH3:28])[CH3:27])[C:16]3=[O:31])=O)(C)(C)C>FC(F)(F)C(O)=O>[CH3:22][C:18]1[N:17]([CH2:23][O:24][C:25](=[O:30])[C:26]([CH3:27])([CH3:28])[CH3:29])[C:16](=[O:31])[C:15]2[C:20](=[CH:21][C:12]3[CH2:11][CH2:10][CH:9]([NH:8][C:32]4[CH:33]=[CH:34][C:35]([C:38]([O:40][CH3:41])=[O:39])=[N:36][CH:37]=4)[C:13]=3[CH:14]=2)[N:19]=1

Participants

3

Reactant 1

HCID 19066354HCID 19066354, compound

Product 1

HCID 19066330HCID 19066330, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of methyl 5-[N-(tert-butoxycarbonyl)-N-((6RS)-2-methyl-4-oxo-3-pivaloyloxymethyl-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl)amino]pyridine-2-carboxylate (0.3 g) and trifluoroacetic acid (10 ml) was stirred at ambient temperature for 1 hour. 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 hexane and ethyl acetate as eluant. There was thus obtained methyl 5-[N-((6RS)-2-methyl-4-oxo-3-pivaloyloxymethyl-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl)amino]pyridine-2-carboxylate (0.24 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 hexane and ethyl acetate as eluant

Sources & evidence

ORD record
ord-bfb676b462fc4622a0c5174dc97bdc63
Source dataset
uspto-grants-1998_05
Patent number
US05747499

Reaction notes

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