Hydrochloric Acid → HCID 70155021, compound

HRID 2187071Notes

Reaction equation

HRID 2187071 reaction equation
[ClH:1].[O:2]=[C:3]1[N:12]([CH2:13][C:14]([OH:16])=[O:15])[C:11](=[O:17])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]1[CH2:18][CH2:19][CH2:20][CH2:21][N:22]1[CH2:27][CH2:26][CH:25]([O:28][CH:29]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH2:24][CH2:23]1.C(N(CC)CC)C.Br[CH2:50][C:51]([O:53][CH3:54])=[O:52]>O.CN(C)C=O>[ClH:1].[O:2]=[C:3]1[N:12]([CH2:13][C:14]([O:16][CH2:50][C:51]([O:53][CH3:54])=[O:52])=[O:15])[C:11](=[O:17])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]1[CH2:18][CH2:19][CH2:20][CH2:21][N:22]1[CH2:23][CH2:24][CH:25]([O:28][CH:29]([C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)[C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH2:26][CH2:27]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 60984Methyl bromoacetateHCID 17795908HCID 17795908, compound

Product 1

HCID 70155021HCID 70155021, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of the hydrochloride of 2,4-dioxo-1-[4-(4-diphenylmethoxypiperidino)butyl]-1,2,3,4-tetrahydroquinazoline-3-acetic acid obtained in Example 50 (0.58 g, 1.00 mmol), triethylamine (0.42 ml, 3.00 mmol) and N,N-dimethylformamide (2.0 ml) was stirred at 60° C. for 15 minutes, and methyl bromoacetate (0.11 ml, 1.20 mmol) was added dropwise. The reaction mixture was stirred at the same temperature for 6 hours, combined with an iced water, and then extracted with a solvent mixture of ethyl ether-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 chloroform-methanol (20:1, v/v) to give a free form of the title compound (0.49 g, 80%) as an oil.

Workup

  1. stirringThe reaction mixture was stirred at the same temperature for 6 hours
  2. extractionextracted with a solvent mixture of ethyl ether-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-0b96772b46154370940621529d6155b0
Source dataset
uspto-grants-2002_06
Patent number
US06407116B1

Reaction notes

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