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

HRID 1633971Notes

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.[C:17]([C:21]1[CH:27]=[CH:26][C:24]([NH2:25])=[CH:23][CH:22]=1)([CH3:20])([CH3:19])[CH3:18].C(O)(=O)C.C([BH3-])#N.[Na+]>CN(C=O)C.COC(OC)OC.CO>[C:17]([C:21]1[CH:22]=[CH:23][C:24]([NH:25][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)=[CH:26][CH:27]=1)([CH3:20])([CH3:18])[CH3:19]

Participants

Conditions

Temperature: 25 °C

Procedure

The above resin bound 4-formyl-N-(2H-tetrazol-5-yl)benzamide (500 mg) was treated with a 0.5 M solution of 4-tert-butylaniline (2.5 mmol, 412.5 mg) in a mixture of DMF and trimethylorthoformate (1:1, 5 mL) and glacial acetic acid (500 μL) for 1 hour at 25° C. followed by sodium cyanoborohydride (2.5 mmol, 160 mg) dissolved in a mixture of DMF and methanol (1:1, 2.5 mL). Shaking at 25° C. for 4 hours followed by filtration and washing with a mixture of methanol and DMF (1:1, 2×10 mL), DMF(3×10 mL) and dichloromethane (2×10 mL) afforded the desired product.

Workup

filtrationfollowed by filtration
washwashing with a mixture of methanol and DMF (1:1, 2×10 mL), DMF(3×10 mL) and dichloromethane (2×10 mL)

Sources & evidence

ORD record: ord-ac20aac5f5fe472dbe9e5056dd2058ad
Source dataset: uspto-grants-2003_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06503949B1

Reaction notes

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