Diisopropylethylamine → HCID 86720537, compound

HRID 1755248Notes

Reaction equation

HRID 1755248 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]([O:14]CC)=O)[N:6]=[CH:5]2.[NH2:17][C@H:18]1[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19]1.C(N(C(C)C)CC)(C)C>CN1C(=O)CCC1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]([NH:17][C@H:18]1[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19]1)=[O:14])[N:6]=[CH:5]2

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 854071tert-butyl (3S)-3-aminopyrrolidine-1-carboxylateHCID 86720535HCID 86720535, compound

Product 1

HCID 86720537HCID 86720537, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of ethyl 6-chloroquinazoline-2-carboxylate (0.200 g, 0.85 mmol, 1 eq) in 0.42 mL of NMP was added (S)-tert-butyl 3-aminopyrrolidine-1-carboxylate (0.16 g, 0.86 mmol, 1 eq) and diisopropylethylamine (0.6 mL, 3.4 mmol, 4 eq). After stirring at 150° C. for 20 h, the mixture was concentrated and purified via silica gel flash chromatography to provide (S)-tert-butyl 3-(6-chloroquinazoline-2-carboxamido)pyrrolidine-1-carboxylate (0.08 g, 0.21 mmol, 25%).

Workup

  1. concentrationthe mixture was concentrated
  2. custompurified via silica gel flash chromatography

Sources & evidence

ORD record
ord-a2f769df97ec4423aa223ed364c9040f
Source dataset
uspto-grants-2015_10
Patent number
US09169261B2

Reaction notes

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