Methyl 3-isocyanatobenzoate → 3-{3-(4-tert-Butylphenyl)-3-[4-(2H-tetrazol-5-ylcarbamoyl)benzyl]ureido}benzoic acid

HRID 1814693Notes

Reaction equation

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

Participants

Conditions

Temperature: 25 °C

Procedure

2.50 mmol 3-isocyanatobenzoic acid methyl ester dissolved in 5 mL dichloroethane was added to the above resin 4-[(4-tert-butylphenylamino)methyl]-N-(2H-tetrazol-5-yl)benzamide (500 mg). Shaking the mixture 5 hours at 25° C. followed by filtration and washing of the resin with dichloromethane (2×10 mL), DMF (2× mL) and THF (3×10 mL) afforded the resin bound title compound.

Workup

filtrationfollowed by filtration
washwashing of the resin with dichloromethane (2×10 mL), DMF (2× mL) and THF (3×10 mL)
customafforded the resin

Sources & evidence

ORD record: ord-d4c04a6a875549e7aa4a67e2b975197f
Source dataset: uspto-grants-2005_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06875760B2

Reaction notes

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