Diisopropylethylamine → HCID 131735417, compound

HRID 631389Notes

Reaction equation

COC1C=C2C(=CC=1OC)N=C[N:7]=C2SC1C=C(C=CC=1)N.[CH3:23][O:24][C:25]1[CH:26]=[C:27]([NH:35][C:36](=[O:44])OC2C=CC=CC=2)[CH:28]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:30]=1.C(N(C(C)C)CC)(C)C>C1COCC1.CN(C)C1C=CN=CC=1.CCOC(C)=O>[CH3:23][O:24][C:25]1[CH:26]=[C:27]([NH:35][C:36](=[O:44])[NH2:7])[CH:28]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:30]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To 3-(6,7-dimethoxyquinazolin-4-ylthio)aniline from the previous step (94 mg, 0.3 mmol) in THF (3 mL) was added phenyl 3-methoxy-5-(trifluoromethyl)phenylcarbamate from Example 115A (140 mg, 0.45 mmol), diisopropylethylamine (80 uL, 0.45 mmol), and 4-dimethylaminopyridine (4 mg, 0.03 mmol). The solution was stirred at 50° C. overnight, allowed to cool to room temperature, and diluted with EtOAc. The solid was then filtered to give 14346,7-dimethoxyquinazolin-4-ylthio)phenyl)-3-(3-methoxy-5-(trifluoromethyl)phenyl)urea (89 mg, 0.17 mmol, 56%). 1H NMR (300 MHz, DMSO-d6) δ 9.12 (s, 1H), 9.02 (s, 1H), 8.70 (s, 1H), 7.84 (s, 1H), 7.55 (d, 1H), 7.48 (s, 1H), 7.44 (t, 1H), 7.35 (s, 1H), 7.34 (s, 1H), 7.29-7.24 (m, 2H), 6.85 (s, 1H), 3.99 (s, 6H), 3.81 (s, 3H); LC-MS (ESI) m/z 531 (M+H)+.

Workup

temperatureto cool to room temperature
filtrationThe solid was then filtered

Sources & evidence

ORD record: ord-bd4cdde04bec4aee9f92745ba6457a5d
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09320739B2

Reaction notes

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