Acetic Acid → HCID 22449844, compound

HRID 2187065Notes

Reaction equation

HRID 2187065 reaction equation
N[C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:37])[NH:7][C:8](=[O:36])[N:9]2[CH2:12][CH2:13][CH2:14][CH2:15][N:16]2[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]2)=[CH:4][CH:3]=1.[C:38](O)(=O)C.C=O.[C:44]([BH3-])#[N:45].[Na+]>CO>[CH3:38][N:45]([CH3:44])[C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:37])[NH:7][C:8](=[O:36])[N:9]2[CH2:12][CH2:13][CH2:14][CH2:15][N:16]2[CH2:17][CH2:18][CH:19]([O:22][CH:23]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH2:20][CH2:21]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 22449621HCID 22449621, compound

Product 1

HCID 22449844HCID 22449844, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

7-Amino-2,4-dioxo-1-[4-(4-diphenylmethoxypiperidino)butyl]-1,2,3,4-tetrahydroquinazoline (500 mg) obtained in Example 39 was suspended in methanol (5.00 ml), and to this mixture acetic acid (0.5 ml) and 37% formaldehyde (0.5 ml) were added and the mixture was stirred for 1 hour. A solution of sodium cyanoborohydride (94.5 mg) in methanol (2.0 ml) was added dropwise and the mixture was stirred at room temperature for 21 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 to give the title compound (378 mg, 72%) from a fraction eluted with n-hexane-ethyl acetate (5:1,v/v). Recrystallization from ethyl acetate-ethyl ether yielded a yellow crystal having a melting point of 203 to 204° C.

Workup

  1. stirringthe mixture was stirred at room temperature for 21 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-1ab4decf2844443ea3f3eff73ee8e518
Source dataset
uspto-grants-2002_06
Patent number
US06407116B1

Reaction notes

Loading…