3-(6-Methoxy-7-(2-morpholinoethoxy)quinazolin-4-yloxy)aniline → 1-(4-Methoxy-3-(trifluoromethyl)phenyl)-3-(3-(6-methoxy-7-(2-morpholinoethoxy)quinazolin-4-yloxy)phenyl)urea

HRID 631564Notes

Reaction equation

HRID 631564 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1)[N:9]=[CH:8][N:7]=[C:6]2[O:22][C:23]1[CH:24]=[C:25]([CH:27]=[CH:28][CH:29]=1)[NH2:26].[CH3:30][O:31][C:32]1[CH:37]=[CH:36][C:35]([NH:38][C:39](=O)[O:40]C2C=CC=CC=2)=[CH:34][C:33]=1[C:48]([F:51])([F:50])[F:49]>CN(C)C1C=CN=CC=1>[CH3:30][O:31][C:32]1[CH:37]=[CH:36][C:35]([NH:38][C:39]([NH:26][C:25]2[CH:27]=[CH:28][CH:29]=[C:23]([O:22][C:6]3[C:5]4[C:10](=[CH:11][C:12]([O:13][CH2:14][CH2:15][N:16]5[CH2:21][CH2:20][O:19][CH2:18][CH2:17]5)=[C:3]([O:2][CH3:1])[CH:4]=4)[N:9]=[CH:8][N:7]=3)[CH:24]=2)=[O:40])=[CH:34][C:33]=1[C:48]([F:49])([F:50])[F:51]

Participants

4

Reactant 2

HCID 668766313-(6-Methoxy-7-(2-morpholinoethoxy)quinazolin-4-yloxy)anilineHCID 66876756Phenyl 4-methoxy-3-(trifluoromethyl)phenylcarbamate

Product 1

HCID 582679331-(4-Methoxy-3-(trifluoromethyl)phenyl)-3-(3-(6-methoxy-7-(2-morpholinoethoxy)quinazolin-4-yloxy)phenyl)ureaYield 27%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

Using the procedure described in Example 230B 3-(6-methoxy-7-(2-morpholinoethoxy)quinazolin-4-yloxy)aniline (90 mg, 0.23 mmol) was reacted with phenyl 4-methoxy-3-(trifluoromethyl)phenylcarbamate described in Example 138A (99 mg, 0.32 mmol) and 4-(dimethylamino)pyridine (28 mg, 0.23 mmol) to give 1-(4-methoxy-3-(trifluoromethyl)phenyl)-3-(3-(6-methoxy-7-(2-morpholinoethoxy)quinazolin-4-yloxy)phenyl)urea (38.72 mg, 27%) as a white solid. 1H NMR (300 MHz, DMSO-d6) δ 8.92 (bs, 1H), 8.85 (bs, 1H), 8.56 (s, 1H), 7.60-7.51 (m, 3H), 7.43-7.35 (m, 2H), 7.26-7.19 (m, 2H), 6.92 (d, 1H), 4.33 (bs, 2H), 3.99 (s, 3H), 3.84 (s, 2H), 3.61 (s, 4H), 2.90-2.69 (m, 2H), 2.65-2.55 (m, 2H); LC-MS (ESI) m/z 614 (M+H)+.

Sources & evidence

ORD record
ord-c66607ca487741458d7f235afb400ebe
Source dataset
uspto-grants-2016_04
Patent number
US09320739B2

Reaction notes

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