Diisopropylethylamine → HCID 54264319, compound

HRID 1288839Notes

Reaction equation

HRID 1288839 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.[CH:17]([N:20]([CH:23]([CH3:25])[CH3:24])[CH2:21][CH3:22])([CH3:19])[CH3:18].C[O:27][C:28](=[O:34])[C@@H:29]1[CH2:33][CH2:32][CH2:31][NH:30]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:20]2[CH2:21][CH2:22][CH2:25][C@H:23]2[CH2:24][C:28]([OH:34])=[O:27])[N:3]=1.[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]([C:17]([N:30]2[CH2:31][CH2:32][CH2:33][C@H:29]2[C:28]([OH:27])=[O:34])([CH3:19])[CH3:18])[N:3]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 902352-Chloro-6,7-dimethoxy-4-quinazolinamineHCID 853477Methyl L-prolinate

Product 2

HCID 54264319HCID 54264319, compoundHCID 86752498HCID 86752498, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 4-amino-2-chloro-6,7-dimethoxyquinazoline (92.8 mg, 0.387 mmol), diisopropylethyl amine (50 mg, 0.387), and (S)-proline methyl ester (50.0 mg, 0.387 mol) in 2-propanol (1 mL) was heated at 90° C. (24 h). The solvent was removed in vacuo and the residue subjected to preparative HPLC Water Delta Prep 4000 (C18, isocratic 50% CH3CN [0.1% TFA]-50% H2O [0.1% TFA]) to afford (S)-1-(4-Amino-6,7-dimethoxy-2-quinazolinyl)-2-carboxymethyl pyrrolidine and (S)-1-(4-Amino-6,7-dimethoxy-2-quinazolinyl)-2-carboxyisopropyl pyrrolidine. For (S)-1-(4-Amino-6,7-dimethoxy-2-quinazolinyl)-2-carboxymethyl pyrrolidine:

Workup

  1. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-9b8d7e99698c40538611a8b24e5832a4
Source dataset
uspto-grants-1998_05
Patent number
US05747490

Reaction notes

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