Acetic Acid → 4-[(4-cyclohexylphenylamino)methyl]-N-(2H-tetrazol-5-yl)benzamide

HRID 1633930Notes

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

Participants

Conditions

Temperature: 70 °C

Procedure

4-Formyl-N-(2H-tetrazol-5-yl)benzamide (8.94 g, 41.2 mmol) was dissolved in DMF (50 mL) by gentle heating. A solution of 4-cyclohexylaniline (7.20 g, 41.2 mmol) in methanol (100 mL) was added and a turbid suspension was formed. The suspension was heated to 70° C. for 1 hour. Acetic acid (50 mL) and sodium cyanoborohydride (2.0 g, 31.7 mmol) was then added. The turbid suspension was heated to 70° C. for an additional hour, before being cooled to 0° C. on an ice bath. The insoluble material was collected by filtration and washed twice with water, before being dried overnight in a vacuum oven to afford 12.94 g (83.5%) of 4-[(4-cyclohexylphenylamino)methyl]-N-(2H-tetrazol-5-yl)benzamide.

Workup

customa turbid suspension was formed
temperatureThe turbid suspension was heated to 70° C. for an additional hour
temperaturebefore being cooled to 0° C. on an ice bath
filtrationThe insoluble material was collected by filtration
washwashed twice with water
custombefore being dried overnight in a vacuum oven

Sources & evidence

ORD record: ord-5c17fc4a9de0444992340c3ee9731d22
Source dataset: uspto-grants-2003_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06503949B1

Reaction notes

Loading…