2-Chloro-6,7-dimethoxy-4-quinazolinamine → Benzyl (2S)-4-(4-amino-6,7-dimethoxy-2-quinazolinyl)-2-[(2-methyl-2-propanyl)carbamoyl]-1-piperazinecarboxylate

HRID 1288835Notes

Reaction equation

HRID 1288835 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[C:4](Cl)[N:3]=1.[CH2:17]([O:24][C:25]([N:27]1[CH2:32][CH2:31][NH:30][CH2:29][C@H:28]1[C:33]([NH:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])=[O:26])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CC(O)C>[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[C:4]([N:30]2[CH2:31][CH2:32][N:27]([C:25]([O:24][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[O:26])[C@H:28]([C:33]([NH:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:29]2)[N:3]=1

Participants

4

Reactant 2

HCID 902352-Chloro-6,7-dimethoxy-4-quinazolinamineHCID 10757986HCID 10757986, compound

Product 1

HCID 6603904Benzyl (2S)-4-(4-amino-6,7-dimethoxy-2-quinazolinyl)-2-[(2-methyl-2-propanyl)carbamoyl]-1-piperazinecarboxylate

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 4-amino-2-chloro-6,7-dimethoxyquinazoline (0.78 g, 3.2535 mmol) and (S)-4-[(benzyloxy)carbonyl]-3-(1,1-dimethylethylamino) carbonyl piperazine (see Askin, D. et al., Tetrahedron Letters 1994, 35, 673-676) (1.04 g, 3.2535 mmol) in 2-propanol (6 mL) was heated at 90° C. (24 h). The solvent was removed in vacuo and the residue subjected to SGC (SiO2, 40 mm×240 mm, 0-10% MeOH/CH2Cl2) which afforded (S)-1-(4-Amino-6,7-dimethoxy-2-quinazolinyl)-4-[(benzyloxy)carbonyl]-3-(1,1-dimethylethylamino)carbonyl piperazine.

Workup

  1. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-93f56c5ad2da4a54b4bdec2c44f6ff29
Source dataset
uspto-grants-1998_05
Patent number
US05747490

Reaction notes

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