Ethanol → HCID 68579415, compound

HRID 1373303Notes

Reaction equation

[Cl:1][C:2]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][C:3]=1[NH:4][C:5]1[C:14]2[C:9](=[CH:10][C:11]([O:22][CH2:23][C@@H:24]3[O:26][CH2:25]3)=[CH:12][C:13]=2[O:15][CH:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)[N:8]=[CH:7][N:6]=1.[NH:33]1[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1.C(O)C>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][C:3]=1[NH:4][C:5]1[C:14]2[C:9](=[CH:10][C:11]([O:22][CH2:23][C@H:24]([OH:26])[CH2:25][N:33]3[CH2:38][CH2:37][O:36][CH2:35][CH2:34]3)=[CH:12][C:13]=2[O:15][CH:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)[N:8]=[CH:7][N:6]=1

Participants

Conditions

Temperature: 45 °C

Procedure

A mixture of 4-(2-chloro-5-methoxyanilino)-7-[(2R)-2,3-epoxypropoxy]-5-tetrahydropyran-4-yloxyquinazoline (0.08 g), morpholine (0.044 ml), ethanol (1 ml) and chloroform (1 ml) was stirred and heated to 45° C. for 16 hours. The mixture was cooled to ambient temperature and evaporated. The residue was triturated under pentane. The resultant solid was isolated, washed with diethyl ether and dried under vacuum to give the title compound (0.08 g); NMR Spectrum: (DMSOd6 and CF3CO2D) 1.9–2.05 (m, 2H), 2.15 (d, 2H), 3.1–3.45 (m, 5H), 3.45–3.6 (m, 3H), 3.7–3.9 (m, 2H), 3.8 (s, 3H), 3.9–4.1 (m, 2H), 4.22 m, 1H), 4.45 (m, 1H), 5.15 (m, 1H), 6.95 (s, 1H), 7.02 (m, 1H), 7.15 (s, 1H), 7.5–7.6 (m, 2H), 8.9 (s, 1H); Mass Spectrum: M+H+ 545 and 547.

Workup

temperatureThe mixture was cooled to ambient temperature
customevaporated
customThe residue was triturated under pentane
customThe resultant solid was isolated
washwashed with diethyl ether
customdried under vacuum

Sources & evidence

ORD record: ord-c4e0c9d4d0444d28a0ebf6c07115ec5b
Source dataset: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07160891B2

Reaction notes

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