Acetic Acid → HCID 67690317, compound

HRID 1289234Notes

Reaction equation

HRID 1289234 reaction equation
[CH3:1][C:2]1[N:11]([O:12][C:13](=[O:18])[C:14]([CH3:17])([CH3:16])[CH3:15])[C:10](=[O:19])[C:9]2[C:4](=[CH:5][C:6]3[CH2:23][CH2:22][CH:21]([NH:24][C:25]4[CH:26]=[CH:27][C:28]([C:31]([O:33][CH3:34])=[O:32])=[N:29][CH:30]=4)[C:7]=3[C:8]=2[CH3:20])[N:3]=1.C=O.[C:37](O)(=O)C.C([BH3-])#N.[Na+]>O>[CH3:37][N:24]([C:25]1[CH:26]=[CH:27][C:28]([C:31]([O:33][CH3:34])=[O:32])=[N:29][CH:30]=1)[CH:21]1[C:7]2[C:8]([CH3:20])=[C:9]3[C:4](=[CH:5][C:6]=2[CH2:23][CH2:22]1)[N:3]=[C:2]([CH3:1])[N:11]([O:12][C:13](=[O:18])[C:14]([CH3:15])([CH3:16])[CH3:17])[C:10]3=[O:19]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 67690667HCID 67690667, compound

Product 1

HCID 67690317HCID 67690317, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of methyl 5-[-((6RS)-2-methyl-4-oxo-3-pivaloyloxy-methyl-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl)amino]-pyridine-2-carboxylate (0.24 g), an aqueous solution of formaldehyde (37% weight/volume, 0.52 ml) and glacial acetic acid (5 ml) was stirred at ambient temperature for 30 minutes. Sodium cyanoborohydride (0.05 g) was added portionwise during 5 minutes and the mixture was stirred at ambient temperature for 30 minutes. The mixture was poured onto a mixture of ice and water (20 ml) and extracted with ethyl acetate. The organic phase was dried (MgSO4) and evaporated. The residue was purified by column chromatography using ethyl acetate as eluant. There was thus obtained methyl 5-[N-methyl-N-((6RS)-2-methyl-4-oxo-3-pivaloyloxymethyl-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl)amino]pyridine-2-carboxylate as a gum (0.185 g);

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic phase was dried (MgSO4)
  3. customevaporated
  4. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-a2b2fa8d1e1a44eabdfffd8c57a6f1b4
Source dataset
uspto-grants-1998_05
Patent number
US05747499

Reaction notes

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