Dimethylamine → 1-(4-{2-[7-(3-Dimethylamino-propoxy)-quinazolin-4-ylamino]-ethyl}-phenyl)-3-phenyl-urea

HRID 1468989Notes

Reaction equation

HRID 1468989 reaction equation
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:15]=[C:14]2[C:9]([C:10]([NH:16][CH2:17][CH2:18][C:19]3[CH:24]=[CH:23][C:22]([NH:25][C:26]([NH:28][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)=[O:27])=[CH:21][CH:20]=3)=[N:11][CH:12]=[N:13]2)=[CH:8][CH:7]=1.[CH3:35][NH:36][CH3:37]>CN(C=O)C>[CH3:35][N:36]([CH3:37])[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:15]=[C:14]2[C:9]([C:10]([NH:16][CH2:17][CH2:18][C:19]3[CH:24]=[CH:23][C:22]([NH:25][C:26]([NH:28][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)=[O:27])=[CH:21][CH:20]=3)=[N:11][CH:12]=[N:13]2)=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 592687751-(4-{2-[7-(3-Chloro-propoxy)-quinazolin-4-ylamino]-ethyl}-phenyl)-3-phenyl-urea

Product 1

HCID 451026001-(4-{2-[7-(3-Dimethylamino-propoxy)-quinazolin-4-ylamino]-ethyl}-phenyl)-3-phenyl-ureaYield 49.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1-(4-{2-[7-(3-chloro-propoxy)-quinazolin-4-ylamino]-ethyl}-phenyl)-3-phenyl-urea (20 mg, 0.042 mmol) and dimethylamine (94.7 mg, 0.840 mmol) in DMF (1 mL) was heated at 150° C. in CEM microwave for 10 min. The reaction mixture was purified using silica gel preparative thin layer chromatography to provide the title compound (10 mg, 49%). 1H-NMR (400 MHz, DMSO-d6): δ 8.69 (s, 1H), 8.66 (s, 1H), 8.41 (s, 1H), 8.19 (t, 1H, NH), 8.10-8.12 (m, 1H), 7.43-7.45 (m, 2H), 7.36-7.38 (m, 2H), 7.26 (t, 2H), 7.17 (d, J=8.8 Hz, 2H), 7.08-7.11 (m, 1H), 7.05 (d, J=2.4 Hz, 1H), 6.95 (t, 1H), 4.13 (t, 2H), 3.69 (q, 2H), 2.89 (t, 2H), 2.44 (t, 2H), 2.20 (s, 6H), 1.89-1.93 (m, 2H). LC-MS (ESI) m/z 485.3 (M+1).

Workup

  1. customThe reaction mixture was purified

Sources & evidence

ORD record
ord-f5e96ae6839847bd80354644b913ba34
Source dataset
uspto-grants-2015_04
Patent number
US09006252B2

Reaction notes

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