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

HRID 1633975Notes

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]([CH:21]1[CH2:26][CH2:25][CH:24]([NH2:27])[CH2:23][CH2:22]1)([CH3:20])([CH3:19])[CH3:18].C(O)(=O)C.C([BH3-])#N.[Na+]>CN1C(=O)CCC1.COC(OC)OC.CO>[C:17]([CH:21]1[CH2:22][CH2:23][CH:24]([NH: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)[CH2:25][CH2:26]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 (50 mg) was treated with a 0.5 M solution of 4-tert-butylcyclohexylamine (0.25 mmol, 38.75 mg) in a mixture of NMP 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 NMP and methanol (1:1, 0.25 mL). Shaking at 25° C. for 4 hours followed by filtration and washing with a mixture of NMP and methanol (1:1, 2×1 mL), NMP (3×1 mL) and a mixture of 1,2-dichloropropane (DCP) and diisopropylethylamine (7:1, 2×1 mL) afforded the desired product.

Workup

filtrationfollowed by filtration
washwashing with a mixture of NMP and methanol (1:1, 2×1 mL), NMP (3×1 mL)
additiona mixture of 1,2-dichloropropane (DCP) and diisopropylethylamine (7:1, 2×1 mL)

Sources & evidence

ORD record: ord-58ba27b381b54005aa08ae67793e89f5
Source dataset: uspto-grants-2003_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06503949B1

Reaction notes

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