Dopac → HCID 21851548, compound

HRID 617181

Reaction equation

HRID 617181 reaction equation
[NH2:1][C:2]1[N:11]=[C:10]([CH:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[OH:18][C:19]1[CH:20]=[C:21]([CH2:26][C:27](O)=[O:28])[CH:22]=[CH:23][C:24]=1[OH:25]>CN(C)C1C=CN=CC=1.CN(C)C=O>[NH2:1][C:2]1[N:11]=[C:10]([CH:12]2[CH2:17][CH2:16][N:15]([C:27](=[O:28])[CH2:26][C:21]3[CH:22]=[CH:23][C:24]([OH:25])=[C:19]([OH:18])[CH:20]=3)[CH2:14][CH2:13]2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

5

Reactant 2

HCID 547DopacHCID 15428775HCID 15428775, compound

Product 1

HCID 21851548HCID 21851548, compoundYield 60.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

To an ice-cold solution of 2-amino-4-(4-piperidinyl)quinazoline (600 mg, 2.63 mmol) obtained in example 11(1), 3,4-dihydroxyphenylacetic acid (530 mg, 3.16 mmol) and 4-dimethylaminopyridine (386 mg, 3.16 mmol) in dimethylformamide (20 ml) was added 1-ethyl-3-(N,N'-dimethylaminopropyl)carbodiimide hydrochloride (605 mg, 3.16 mmol) under a nitrogen atmosphere. The mixture was stirred overnight at room temperature. The solvent was removed in vacuo and the residue was crystallized from methanol to give the titled compound (599 mg).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was crystallized from methanol

Sources & evidence

ORD record
ord-1a25b87a62d743c3ad64eaa5fa0c8dcd
Source dataset
uspto-grants-1999_09
Patent number
US05948786

Linked notes

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