Phenyl isocyanate → 1-(4-{2-[7-(3-Chloro-propoxy)-quinazolin-4-ylamino]-ethyl}-phenyl)-3-phenyl-urea

HRID 1468988Notes

Reaction equation

HRID 1468988 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH:10][C:11]2[C:20]3[C:15](=[CH:16][C:17]([O:21][CH2:22][CH2:23][CH2:24][Cl:25])=[CH:18][CH:19]=3)[N:14]=[CH:13][N:12]=2)=[CH:4][CH:3]=1.[C:26]1([N:32]=[C:33]=[O:34])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C(Cl)Cl>[Cl:25][CH2:24][CH2:23][CH2:22][O:21][C:17]1[CH:16]=[C:15]2[C:20]([C:11]([NH:10][CH2:9][CH2:8][C:5]3[CH:6]=[CH:7][C:2]([NH:1][C:33]([NH:32][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)=[O:34])=[CH:3][CH:4]=3)=[N:12][CH:13]=[N:14]2)=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 67218600[2-(4-Amino-phenyl)-ethyl]-[7-(3-chloro-propoxy)-quinazolin-4-yl]-amine

Product 1

HCID 592687751-(4-{2-[7-(3-Chloro-propoxy)-quinazolin-4-ylamino]-ethyl}-phenyl)-3-phenyl-ureaYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of [2-(4-amino-phenyl)-ethyl]-[7-(3-chloro-propoxy)-quinazolin-4-yl]-amine (34 mg, 0.095 mmol) and phenyl isocyanate (17.0 mg, 0.143 mmol) in methylene chloride (8 mL) was stirred under nitrogen at room temperature overnight. The solid product formed was filtered to give the title compound as a solid (42 mg, 93%). 1H-NMR (300 MHz, d6-DMSO): δ 8.66 (s, 1H), 8.63 (s, 1H), 8.42 (s, 1H), 8.20 (t, 1H), 8.13 (d, J=9.0 Hz, 1H), 7.42-7.46 (m, 2H), 7.37 (d, J=8.4 Hz, 2H), 7.24-7.29 (m, 2H), 7.08-7.18 (m, 4H), 6.96 (t, 1H), 4.23 (t, 2H), 3.83 (t, 2H), 3.70 (q, 2H), 2.89 (t, 2H), 2.18-2.27 (m, 2H). LC-MS (ESI) m/z: 476.4 (M+1).

Workup

  1. customThe solid product formed
  2. filtrationwas filtered

Sources & evidence

ORD record
ord-11a89d99c99e4a4a8e8514271301affd
Source dataset
uspto-grants-2015_04
Patent number
US09006252B2

Reaction notes

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