Acetic Acid → HCID 69240704, compound

HRID 2237596Notes

Reaction equation

Cl[C:2]1[N:11]=[C:10]([NH:12][C@H:13]2[CH2:18][CH2:17][CH2:16][CH2:15][C@H:14]2[NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH3:27])[CH:8]=2)[N:3]=1.[CH3:28][O:29][C:30]1[CH:37]=[CH:36][C:33]([CH2:34][NH2:35])=[CH:32][CH:31]=1.C(O)(=O)C>CN1CCCC1=O.CN(C)C1C=CN=CC=1>[CH3:28][O:29][C:30]1[CH:37]=[CH:36][C:33]([CH2:34][NH:35][C:2]2[N:11]=[C:10]([NH:12][C@H:13]3[CH2:18][CH2:17][CH2:16][CH2:15][C@H:14]3[NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:23])[CH3:24])[C:9]3[C:4](=[CH:5][CH:6]=[C:7]([CH3:27])[CH:8]=3)[N:3]=2)=[CH:32][CH:31]=1

Participants

Conditions

Temperature: 110 °C

Procedure

To a solution of 4.00 g of tert-butyl (1R,2S)-2-[(2-chloro-6-methylquinazolin-4-yl)amino]cyclohexylcarbamate and 5.91 g of 4-methoxybenzylamine in 30 ml of N-methyl-2-pyrrolidone, 100 mg of 4-dimethylaminopyridine was added, and then the mixture was stirred at 110° C. for 24 hours. The reaction solvent was mixed with an aqueous 5% acetic acid solution and then extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and then dried. The solvent was distilled off and the residue was purified by silica gel column chromatography (chloroform:methanol=20:1) to obtain 5.10 g of the desirable compound.

Workup

extractionextracted with ethyl acetate
washThe organic layer was washed with water and saturated brine
customdried
distillationThe solvent was distilled off
customthe residue was purified by silica gel column chromatography (chloroform:methanol=20:1)

Sources & evidence

ORD record: ord-f4ba12bd70e94c3aae76be2cd77d0600
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07718663B2

Reaction notes

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