Acetic Acid → HCID 22449904, compound

HRID 2187066Notes

Reaction equation

HRID 2187066 reaction equation
N[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][CH2:13][CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][CH:19]([O:22][CH:23]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:18][CH2:17]1)[C:7](=[O:36])[NH:6][C:5]2=[O:37].[C:38](O)(=O)C.C=O.[C:44]([BH3-])#[N:45].[Na+]>CO>[CH3:38][N:45]([CH3:44])[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][CH2:13][CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][CH:19]([O:22][CH:23]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:18][CH2:17]1)[C:7](=[O:36])[NH:6][C:5]2=[O:37]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 22449735HCID 22449735, compound

Product 1

HCID 22449904HCID 22449904, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

6-Amino-2,4-dioxo-1-[4-(4-diphenylmethoxypiperidino)butyl)-1,2,3,4-tetrahydroquinazoline (800 mg) obtained in Example 40 was suspended in methanol (8.0 ml), and to this mixture acetic acid (0.8 ml) and 37% formaldehyde (0.8 ml) were added and the mixture was stirred for 1.5 hours. A solution of sodium cyanoborohydride (141 mg) in methanol (4.0 ml) was added dropwise and the mixture was stirred at room temperature for 27 hours. The reaction mixture was concentrated under reduced pressure, diluted with ethyl acetate, washed with water, dried (Na2SO4) and then the solvent was distilled off under reduced pressure. The residue was subjected to a column chromatography on a silica gel eluting with n-hexane-ethyl acetate (5:1,v/v) to give the title compound (420 mg, 50%). Recrystallization from ethyl acetate-ethyl ether yielded a yellow crystal having a melting point of 165 to 167° C.

Workup

  1. stirringthe mixture was stirred at room temperature for 27 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additiondiluted with ethyl acetate
  4. washwashed with water
  5. dry with materialdried (Na2SO4)
  6. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-1cd7eb67caf7440fa0d112ff65f641bb
Source dataset
uspto-grants-2002_06
Patent number
US06407116B1

Reaction notes

Loading…