Water → Methyl 4-{[(1R)-1-(3-nitrophenyl)ethyl]amino}quinazoline-8-carboxylate

HRID 474417Notes

Reaction equation

Cl[C:2]1[C:11]2[C:6](=[C:7]([C:12]([O:14][CH3:15])=[O:13])[CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][N:3]=1.C(N(CC)C(C)C)(C)C.Cl.[N+:26]([C:29]1[CH:30]=[C:31]([C@H:35]([NH2:37])[CH3:36])[CH:32]=[CH:33][CH:34]=1)([O-:28])=[O:27].O>C(#N)C>[N+:26]([C:29]1[CH:30]=[C:31]([C@H:35]([NH:37][C:2]2[C:11]3[C:6](=[C:7]([C:12]([O:14][CH3:15])=[O:13])[CH:8]=[CH:9][CH:10]=3)[N:5]=[CH:4][N:3]=2)[CH3:36])[CH:32]=[CH:33][CH:34]=1)([O-:28])=[O:27]

Participants

Conditions

Temperature: 45 °C

Procedure

A suspension of methyl 4-chloroquinazoline-8-carboxylate (7.18 g, 32.25 mmol) in acetonitrile (70 mL), was treated with N,N-diisopropylethylamine (21.69 g, 167.81 mmol, 5 eq), followed by (1R)-1-(3-nitrophenyl)ethanamine hydrochloride (6.80 g, 33.56 mmol). The suspension was warmed to 45° C. and stirred for 4 h. The reaction mixture was slowly added to water (1000 mL) to precipitate an off-white solid. The solid was filtered to get 8.52 g (24.18 mmol, 75%). LCMS: (M+1) 353.

Workup

customto precipitate an off-white solid
filtrationThe solid was filtered
customto get 8.52 g (24.18 mmol, 75%)

Sources & evidence

ORD record: ord-bc51379b4a3f43079a3a33c364f99746
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08637532B2

Reaction notes

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