Triethylamine → HCID 22449822, compound

HRID 2187080Notes

Reaction equation

HRID 2187080 reaction equation
[O:1]=[C:2]1[N:11]([CH2:12][C:13](O)=[O:14])[C:10](=[O:16])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]1[CH2:17][CH2:18][CH2:19][CH2:20][N:21]1[CH2:26][CH2:25][CH:24]([O:27][CH:28]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:23][CH2:22]1.[ClH:41].[CH3:42][O:43][C:44](=[O:47])[CH2:45][NH2:46].C(P(=O)(OCC)OCC)#N.C(N(CC)CC)C>CN(C)C=O>[ClH:41].[O:1]=[C:2]1[N:11]([CH2:12][C:13]([NH:46][CH2:45][C:44]([O:43][CH3:42])=[O:47])=[O:14])[C:10](=[O:16])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]1[CH2:17][CH2:18][CH2:19][CH2:20][N:21]1[CH2:26][CH2:25][CH:24]([O:27][CH:28]([C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH2:23][CH2:22]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 122755Glycine methyl ester hydrochlorideHCID 17795908HCID 17795908, compound

Product 1

HCID 22449822HCID 22449822, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2,4-dioxo-1-[4-(4-diphenylmethoxypiperidino)butyl]-1,2,3,4-tetrahydroquinazoline-3-acetic acid (1.20 g, 2.22 mmol) obtained in Example 50 and glycine methyl ester hydrochloride (278 mg, 2.66 mmol) in N,N-dimethylformamide (20.0 ml), diethyl cyanophosphonate (425 ml, 2.66 mmol) and triethylamine (926 ml, 6.65 mmol) were added sequentially, and then the reaction mixture was stirred at room temperature for 17 hours. The solvent was distilled off under reduced pressure, and the residue was combined with water and extracted with ethyl acetate. After the extract was washed with water and dried (MgSO4), 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 methyl ester of the title compound (883 mg, 65%) as an oil.

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. extractionextracted with ethyl acetate
  3. washAfter the extract was washed with water
  4. dry with materialdried (MgSO4)
  5. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-1380c17f4502492fb2113b9e6fee3347
Source dataset
uspto-grants-2002_06
Patent number
US06407116B1

Reaction notes

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