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

HRID 1814648Notes

Reaction equation

[CH:1]([C:3]1[CH:16]=[CH:15][C:6]([C:7]([NH:9][C:10]2[N:11]=[N:12][NH:13][N:14]=2)=[O:8])=[CH:5][CH:4]=1)=O.[CH:17]1([C:23]2[CH:29]=[CH:28][C:26]([NH2:27])=[CH:25][CH:24]=2)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1.[C:30]([OH:33])(=O)C.[C:34]([BH3-])#[N:35].[Na+]>CN(C=O)C.COC(OC)OC.CO>[C:7]([C:6]1[CH:15]=[C:34]([NH:35][C:30](=[O:33])[N:27]([CH2:1][C:3]2[CH:16]=[CH:15][C:6]([C:7]([NH:9][C:10]3[N:11]=[N:12][NH:13][N:14]=3)=[O:8])=[CH:5][CH:4]=2)[C:26]2[CH:25]=[CH:24][C:23]([CH:17]3[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]3)=[CH:29][CH:28]=2)[CH:3]=[CH:4][CH:5]=1)#[N:9]

Participants

Conditions

Temperature: 25 °C

Procedure

The above resin bound 4-formyl-N-(2H-tetrazol-5-yl)benzamide (50 mg) was treated with a 0.5 M solution of 4-cyclohexylaniline (0.25 mmol, 41.25 mg) in a mixture of DMF and trimethylorthoformate (1:1, 0.5 mL) and glacial acetic acid (50 μL) for 1 hour at 25° C. followed by sodium cyanoborohydride (250 μmol, 16 mg) dissolved in a mixture of DMF and methanol (1:1, 0.25 mL). Shaking at 25° C. for 4 hours followed by filtration and washing with a mixture of DMF and methanol (1:1, 2×1 mL), 3×1 mL DMF and 2×1 mL dichloromethane afforded the desired product.

Workup

filtrationfollowed by filtration
washwashing with a mixture of DMF and methanol (1:1, 2×1 mL), 3×1 mL DMF and 2×1 mL dichloromethane

Sources & evidence

ORD record: ord-94da7343febb491a9a0edc401fa48815
Source dataset: uspto-grants-2005_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06875760B2

Reaction notes

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