3-(6-Methoxy-7-(2-methoxyethoxy)quinazolin-4-ylthio)aniline → HCID 58267893, compound

HRID 871658Notes

Reaction equation

HRID 871658 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][O:16][CH3:17])[N:9]=[CH:8][N:7]=[C:6]2[S:18][C:19]1[CH:20]=[C:21]([CH:23]=[CH:24][CH:25]=1)[NH2:22].[C:26]([C:28]([C:31]1[CH:32]=[C:33]([NH:37][C:38](=O)[O:39]C2C=CC=CC=2)[CH:34]=[CH:35][CH:36]=1)([CH3:30])[CH3:29])#[N:27]>C1COCC1.CN(C1C=CN=CC=1)C>[C:26]([C:28]([C:31]1[CH:32]=[C:33]([NH:37][C:38]([NH:22][C:21]2[CH:23]=[CH:24][CH:25]=[C:19]([S:18][C:6]3[C:5]4[C:10](=[CH:11][C:12]([O:13][CH2:14][CH2:15][O:16][CH3:17])=[C:3]([O:2][CH3:1])[CH:4]=4)[N:9]=[CH:8][N:7]=3)[CH:20]=2)=[O:39])[CH:34]=[CH:35][CH:36]=1)([CH3:30])[CH3:29])#[N:27]

Participants

5

Reactant 2

HCID 668767643-(6-Methoxy-7-(2-methoxyethoxy)quinazolin-4-ylthio)anilineHCID 66877200Phenyl 3-(2-cyanopropan-2-yl)phenylcarbamate

Product 1

HCID 58267893HCID 58267893, compoundYield 23%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Using the procedure described in Example 278B, to a solution of 3-(6-methoxy-7-(2-methoxyethoxy)quinazolin-4-ylthio)aniline (102 mg, 0.3 mmol), prepared as described in Example 230A, in THF (3 ml) was added DMAP (18 mg, 0.15 mmol) and phenyl 3-(2-cyanopropan-2-yl)phenylcarbamate (92 mg, 0.33 mmol) described in Example 278A to afford 1-(3-(2-cyanopropan-2-yl)phenyl)-3-(3-(6-methoxy-7-(2-methoxyethoxy)quinazolin-4-ylthio)phenyl)urea (37.2 mg, 23%) as a solid. 1H NMR (300 MHz, DMSO-d6) δ 1.67 (s, 6H), 3.76 (s, 3H), 4.00 (s, 4H), 4.34 (s, 3H), 7.11 (d, J=6 Hz, 1H), 7.24-7.43 (m, 7H), 7.66 (s, 1H), 7.84 (s, 1H), 8.69 (s, 1H), 8.92 (d, J=9 Hz, 2H); LC-MS (ESI) m/z 544 (M+H)+.

Workup

  1. customprepared

Sources & evidence

ORD record
ord-541377c2cf0044559c7874c1606f5004
Source dataset
uspto-grants-2015_03
Patent number
US08969587B2

Reaction notes

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