Morpholine → HCID 46842156, compound

HRID 1846359Notes

Reaction equation

[CH:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:20](=[O:21])[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]=[C:12]2[C:22]2[CH:23]=[N:24][C:25]([CH2:28]O)=[CH:26][CH:27]=2)=[CH:7][CH:6]=1)([CH2:3][CH3:4])[CH3:2].CCN(C(C)C)C(C)C.CS(Cl)(=O)=O.[NH:44]1[CH2:49][CH2:48][O:47][CH2:46][CH2:45]1>C(Cl)Cl>[CH:1]([C:5]1[CH:6]=[CH:7][C:8]([N:11]2[C:20](=[O:21])[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]=[C:12]2[C:22]2[CH:23]=[N:24][C:25]([CH2:28][N:44]3[CH2:49][CH2:48][O:47][CH2:46][CH2:45]3)=[CH:26][CH:27]=2)=[CH:9][CH:10]=1)([CH2:3][CH3:4])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

3-(4-sec-butylphenyl)-2-(6-(hydroxymethyl)pyridin-3-yl)quinazolin-4(3H)-one (0.176 g, 0.46 mmol) was dissolved in CH2Cl2 (30 mL) under nitrogen and cooled to 0° C. Hünig's base (0.160 mL, 0.92 mmol) was added, followed by MsCl (0.042 mL, 0.55 mmol), and the mixture was stirred for 15 min at 0° C. Morpholine (0.400 mL) was added, the reaction was warmed to room temperature, and stirred for 2 hours, before concentration and purification by flash chromatography on silica gel, eluting with 100% ethyl acetate to 10% methanol/ethyl acetate, afforded the title compound (0.175 g, 984%). 1H-NMR (300 MHz, DMSO-6): δ8.48 (s, 1H), 8.22 (d, J=7.9 Hz, 1H), 7.90-7.95 (m, 1H), 7.79 (d, J=8.1 Hz, 1H), 7.60-7.68 (m, 2H), 7.22-7.27 (m, 3H), 7.10-7.16 (m, 2H), 3.49-3.54 (m, 6H), 2.55-2.63 (m, 1H), 2.19-2.29 (m, 4H), 1.33-1.56 (m, 2H), 1.13 (d, J=6.8 Hz, 3H), 0.62 (t, J=7.2 Hz, 3H). MS (APCI) m/z: 455 (M+H)+.

Workup

temperaturethe reaction was warmed to room temperature
stirringstirred for 2 hours, before concentration and purification by flash chromatography on silica gel
washeluting with 100% ethyl acetate to 10% methanol/ethyl acetate

Sources & evidence

ORD record: ord-ae1be9d80d1a423ba7c8bb0825e9c648
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952021B2

Reaction notes

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