3-Isocyanatobenzonitrile → 4-[3-(3-Cyanophenyl)-1-(4-cyclohexylphenyl)ureidomethyl]-N-(2H-tetrazol-5-yl)benzamide

HRID 1633922Notes

Reaction equation

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

Participants

Conditions

Temperature: 25 °C

Procedure

200 μmol 3-cyanophenylisocyanate dissolved in 500 μL dichloroethane was added to the above resin bound 4-[(4-cyclohexylphenylamino)methyl]-N-(2H-tetrazol-5-yl)benzamide (50 mg). Shaking the mixture for 5 hours at 25° C. followed by filtration and washing of the resin with 2×1 mL dichloromethane, 4×1 mL DMF, 2×1 mL H2O, 3×1 mL THF and 3×1 mL dichloromethane afforded the resin bound title compound.

Workup

additionwas added to the above resin
filtrationfollowed by filtration
washwashing of the resin with 2×1 mL dichloromethane, 4×1 mL DMF, 2×1 mL H2O, 3×1 mL THF and 3×1 mL dichloromethane
customafforded the resin

Sources & evidence

ORD record: ord-e86cb30eec7143a1b15a41fdd5ce845a
Source dataset: uspto-grants-2003_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06503949B1

Reaction notes

Loading…