Pyridine → HCID 57961650, compound

HRID 541948Notes

Reaction equation

F[C:2](F)(F)[C:3](O)=[O:4].[N+:8]([C:11]1[CH:12]=[C:13]([CH:31]=[CH:32][CH:33]=1)[CH2:14][NH:15][CH2:16][C:17]1[CH:18]=[C:19]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH:20]=[CH:21][CH:22]=1)([O-:10])=[O:9].N1C=CC=CC=1.C(OC(=O)C)(=O)C>C(#N)C.CN(C)C1C=CN=CC=1>[C:3]([N:15]([CH2:16][C:17]1[CH:18]=[C:19]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:28])([CH3:29])[CH3:27])[CH:20]=[CH:21][CH:22]=1)[CH2:14][C:13]1[CH:31]=[CH:32][CH:33]=[C:11]([N+:8]([O-:10])=[O:9])[CH:12]=1)(=[O:4])[CH3:2]

Participants

Conditions

Temperature: 20 °C

Procedure

A solution of tert-butyl (3-{[(3-nitrobenzyl)amino]methyl}phenyl)carbamate trifluoroacetate (0.16 g, 0.34 mmol) in acetonitrile (5.2 mL) was treated with 4-dimethylaminopyridine (8.3 mg, 68 μmol), pyridine (0.14 mL, 1.7 mmol), and acetic anhydride (35 μL, 0.37 mmol) and stirred at 20° C. for 16 h. The reaction mixture was purified by preparative LCMS to give the desired product (95 mg, 70%). LCMS for C21H25N3O5Na (M+Na)+: m/z=422.0.

Workup

customThe reaction mixture was purified by preparative LCMS

Sources & evidence

ORD record: ord-0e8d8ed75bd54718ae0824a3135e4a96
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871753B2

Reaction notes

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