Dimethylformamide → HCID 67264261, compound

HRID 1041060Notes

Reaction equation

HRID 1041060 reaction equation
[CH3:1][O:2][C:3]1[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][C:6]2[N:7]([CH3:13])[C:8](=[O:12])[CH2:9][NH:10][CH2:11][C:5]=2[CH:4]=1.Br[CH2:20][C:21]#N.C(N(CC)C(C)C)(C)C.CN(C)C=O>[I-].[Na+]>[CH2:20]([N:10]1[CH2:11][C:5]2[CH:4]=[C:3]([O:2][CH3:1])[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][C:6]=2[N:7]([CH3:13])[C:8](=[O:12])[CH2:9]1)[CH3:21]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11534BromoacetonitrileHCID 81531DiisopropylethylamineHCID 67263977HCID 67263977, compound

Product 1

HCID 67264261HCID 67264261, compoundYield 91.3%

Reagents, catalysts & solvents 1

HCID 5238Sodium IodideCatalyst

Procedure

A mixture of 7-Methoxy-1-methyl-8-nitro-1,3,4,5-tetrahydro-benzo[e][1,4]diazepin-2-one (0.50 g, 0.0020 mol), Sodium iodide (0.0148 g, 0.0000987 mol), Bromoacetonitrile (0.276 mL, 0.00396 mol) and N,N-Diisopropylethylamine (1.04 mL, 0.00597 mol) in N,N-Dimethylformamide (6 mL, 0.08 mol) was reacted in an analogous manner to example 736-E to give 4-Ethyl-7-methoxy-1-methyl-8-nitro-1,3,4,5-tetrahydro-benzo[e][1,4]diazepin-2-one as a tan solid (0.51 g, 88%). Mp129-131° C.; LCMS (m/e) 291 (M+1); 1H-NMR (DMSO, 400 MHz) δ 7.96 (s, 1H), 7.51 (s, 1H), 3.93-92 (s, 3H), 3.86 (s, 2H), 3.82 (s, 2H), 3.27 (s, 3H), 3.16 (s, 2H).

Workup

  1. customwas reacted in an analogous manner to example 736-E

Sources & evidence

ORD record
ord-dca8de2de8494d09b3002fb9c08709ac
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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