Phenyl isocyanate → (+/-)-N-[4-(3-chlorophenyl)-6-[(4-chlorophenyl)hydroxy(1-methyl-1H-imidazol-5-yl)methyl]-2-quinolinyl]-N'-phenylurea

HRID 1827264Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:18]([C:26]4[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=4)([OH:25])[C:19]4[N:23]([CH3:24])[CH:22]=[N:21][CH:20]=4)[CH:16]=3)[N:11]=[C:10]([NH:33][C:34](C3OC=CC=3)=[O:35])[CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[N:41]([C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)=C=O>C1COCC1.O>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:18]([C:26]4[CH:27]=[CH:28][C:29]([Cl:32])=[CH:30][CH:31]=4)([OH:25])[C:19]4[N:23]([CH3:24])[CH:22]=[N:21][CH:20]=4)[CH:16]=3)[N:11]=[C:10]([NH:33][C:34]([NH:41][C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)=[O:35])[CH:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of (±)-2-amino-4-(3-chlorophenyl)-α-(4-chlorophenyl)-α-(1-methyl-1H-imidazol-5-yl)-6-quinolinemethanol (0.000210 mol) (see Example B8) and isocyanato-benzene (0.000630 mol; 3 equiv) in THF (1 ml) was stirred for 5 hours at 60° C. Water (a few drops) was added. The solvent was evaporated. The residue was HPLC purified. The product fractions were collected and the solvent was evaporated, yielding 0.071 g (56.77%) of (±)-N-[4-(3-chlorophenyl)-6-[(4-chlorophenyl)hydroxy(1-methyl-1H-imidazol-5-yl)methyl]-2-quinolinyl]-N′-phenylurea, MS (ESI) m/z: 594 596 598.

Workup

customThe solvent was evaporated
custompurified
customThe product fractions were collected
customthe solvent was evaporated

Sources & evidence

ORD record: ord-09dc9fedffd34107b183feeeccce073e
Source dataset: uspto-grants-2006_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07053105B2

Reaction notes

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