Diisopropylethylamine → HCID 66613954, compound

HRID 1801924Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13](Cl)=[N:14][C:15]([C:19]([C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)=[O:20])=[N:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[CH3:38][C:39]1[NH:43][N:42]=[C:41]([NH2:44])[CH:40]=1>CN(C=O)C.O>[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([NH:44][C:41]3[CH:40]=[C:39]([CH3:38])[NH:43][N:42]=3)=[N:14][C:15]([C:19]([C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)=[O:20])=[N:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 40 °C

Procedure

To (7-(benzyloxy)-4-chloroquinazolin-2-yl)(4-fluorophenyl)methanone (380 mg, 0.97 mmol) in DMF (10 mL) at rt were added DIEA (500 uL, 2.90 mmol), 5-methyl-1H-pyrazol-3-amine (280 mg, 2.90 mmol), and KI (161 mg, 0.97 mmol). After stirring at 40° C. for 18 h, the solution was cooled and diluted with water. After standing at 0° C. for 1 h, the precipitate was collected by filtration and dried under reduced pressure to afford (7-(benzyloxy)-4-(5-methyl-1H-pyrazol-3-ylamino)quinazolin-2-yl)(4-fluorophenyl)methanone as a yellow solid (365 mg, 83%) 1H NMR (300 MHz, DMSO-d6) δ ppm 2.18 (s, 3 H) 5.30 (s, 2 H) 6.48 (s, 1H) 7.33-7.44 (m, 8 H) 7.50-7.52 (m, 2 H) 8.07 (m, 2 H) 8.65 (m, 1 H) 10.53 (s, 1 H) 12.18 (s, 1 H). LC-MS (ESI) m/z 454 (M+H)+

Workup

temperaturethe solution was cooled
waitAfter standing at 0° C. for 1 h
filtrationthe precipitate was collected by filtration
customdried under reduced pressure

Sources & evidence

ORD record: ord-8c2271a7ae94435ab7e547ac9cbec4fb
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08349851B2

Reaction notes

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