HCID 16042898, compound → HCID 16222784, compound

HRID 1695514Notes

Reaction equation

HRID 1695514 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:12][C:11]2[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=2[N:9]=[C:8]([NH2:17])[CH2:7]1)=[O:5])[CH3:2].[N+]([C:21]1C=CC=CC=1CN(CC#N)C(=O)OCC)([O-])=O>>[NH2:17][C:8]1[CH2:7][N:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH:12]([CH3:21])[C:11]2[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=2[N:9]=1

Participants

3

Reactant 2

HCID 16042898HCID 16042898, compoundHCID 59862492HCID 59862492, compound

Product 1

HCID 16222784HCID 16222784, compoundYield 13%

Procedure

This compound was prepared in a similar manner to (E)-ethyl-2-amino-3H-benzo[e][1,4]diazepine-4(5H)-carboxylate (3), substituting ethyl cyanomethyl(1-(2-nitrophenyl)ethyl)carbamate (8) for ethyl-2-nitrobenzyl-(cyanomethyl)carbamate (2), to provide 2.6 mg (0.011 mmol, 13% yield), of the desired product. 1H NMR (400 MHz, CDCl3) δ 1.26 (br s, 3H), 1.40 (d, 3H), 3.45-3.58 (br s, 1H), 4.15-4.29 (m, 2H), 4.44 (br s, 1H), 4.97 (br s, 1H), 7.03-7.06 (m, 2H), 7.18-7.31 (m, 2H).

Workup

  1. customto provide 2.6 mg (0.011 mmol, 13% yield)

Sources & evidence

ORD record
ord-81e134e8cab344e3b3ef20ec6922b5ae
Source dataset
uspto-grants-2012_04
Patent number
US08163738B2

Reaction notes

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