Ethyl Acetate → HCID 59242044, compound

HRID 1876231Notes

Reaction equation

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

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of (3-chloro-4-ethoxy-phenyl)-(2-chloromethyl-quinazolin-4-yl)-methyl-amine (119 mg, 0.328 mmol) and potassium phthalimide (79 mg, 0.43 mmol) in DMF (2 mL) was heated at 50° C. for 3.5 h. EtOAc (25 mL) was added and this was washed with water (4×5 mL) then satd NaCl (2×5 mL). The organic layer was dried (MgSO4), filtered through a pad of silica with an EtOAc wash then concd. The title compound was obtained as an off-white solid (124 mg; 80%) after MPLC (SiO2/0-50% EtOAc in hexanes). 1H NMR (CDCl3) δ 7.96-7.90 (m, 2H), 7.78-7.73 (m, 2H), 7.72 (m, 1H), 7.53 (m, 1H), 7.22 (d, J=2.4 Hz, 1H), 7.05-6.95 (m, 2H), 6.91 (dd, J=2.4, 8.8 Hz, 1H), 6.83 (d, J=8.8 Hz, 1H), 5.14 (s, 2H), 4.10 (q, J=6.9 Hz, 2H), 3.24 (s, 3H), 1.48 (t, J=6.8 Hz, 3H); LC-MS (ESI+; 473 ([M+H]+)).

Workup

washthis was washed with water (4×5 mL)
dry with materialThe organic layer was dried (MgSO4)
filtrationfiltered through a pad of silica with an EtOAc
washwash

Sources & evidence

ORD record: ord-a627ecd34b0442818cf5582d720f77ce
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08309562B2

Reaction notes

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