1-(3-(6,7-Dimethoxyquinazolin-4-yloxy)phenyl)-3-(3-isopropylisoxazol-5-yl)urea → 3-(3-(tetrahydro-2H-pyran-4-yl)isoxazol-5-yl)urea

HRID 631534Notes

Reaction equation

HRID 631534 reaction equation
COC1C=C2C(=CC=1OCCOC)N=C[N:7]=C2OC1C=C(C=CC=1)N.[O:26]1[CH2:31][CH2:30][CH:29]([C:32]2[CH:36]=[C:35]([NH:37][C:38](=[O:46])OC3C=CC=CC=3)[O:34][N:33]=2)[CH2:28][CH2:27]1.COC1C=C2C(=CC=1OC)N=CN=C2OC1C=C(NC(NC2ON=C(C(C)C)C=2)=O)C=CC=1>>[O:26]1[CH2:31][CH2:30][CH:29]([C:32]2[CH:36]=[C:35]([NH:37][C:38](=[O:46])[NH2:7])[O:34][N:33]=2)[CH2:28][CH2:27]1

Participants

4

Reactant 3

HCID 442434351-(3-(6,7-Dimethoxyquinazolin-4-yloxy)phenyl)-3-(3-isopropylisoxazol-5-yl)ureaHCID 668758053-(6-Methoxy-7-(2-methoxyethoxy)quinazolin-4-yloxy)anilineHCID 66876225phenyl 3-(tetrahydro-2H-pyran-4-yl)isoxazol-5-ylcarbamate

Product 1

HCID 909361353-(3-(tetrahydro-2H-pyran-4-yl)isoxazol-5-yl)ureaYield 51.1%

Procedure

Prepared from 3-(6-methoxy-7-(2-methoxyethoxy)quinazolin-4-yloxy)aniline from Example 117B (60 mg, 0.176 mmol) and phenyl 3-(tetrahydro-2H-pyran-4-yl)isoxazol-5-ylcarbamate from Example 123A (56 mg, 0.194 mmol) according to the method described for 1-(3-(6,7-dimethoxyquinazolin-4-yloxy)phenyl)-3-(3-isopropylisoxazol-5-yl)urea in Example 122B to afford 14346-methoxy-7-(2-methoxyethoxy)quinazolin-4-yloxy)phenyl)-3-(3-(tetrahydro-2H-pyran-4-yl)isoxazol-5-yl)urea as a colorless solid (19 mg, 20%). 1H NMR (300 MHz, DMSO-d6) δ 10.70 (brs, 1H), 9.38 (brs, 1H), 8.55 (s, 1H), 7.57 (s, 2H), 7.38-7.42 (m, 2H), 7.32 (m, 1H), 6.98 (m, 1H), 6.00 (s, 1H), 4.34-4.35 (m, 2H), 3.99 (s, 3H), 3.87-3.90 (m, 2H), 3.77-3.78 (m, 2H), 3.42-3.46 (m, 2H), 3.35 (s, 3H), 2.88 (m, 1H), 1.76-1.81 (m, 2H), 1.60-1.65 (m, 2H); LC-MS (ESI) m/z 536 (M+H)+.

Sources & evidence

ORD record
ord-d089f07cfac04ebf95e9daae15d745cb
Source dataset
uspto-grants-2016_04
Patent number
US09320739B2

Reaction notes

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