Ethanol → HCID 86633917, compound

HRID 1687367Notes

Reaction equation

HRID 1687367 reaction equation
[CH3:1][O:2][C:3]1[C:18]([N+:19]([O-])=O)=[CH:17][C:6]2[N:7]([CH3:16])[C:8](=[O:15])[CH2:9][N:10]([CH2:12][C:13]#[N:14])[CH2:11][C:5]=2[CH:4]=1.O.NN.C(O)C>[Pd]>[NH2:19][C:18]1[C:3]([O:2][CH3:1])=[CH:4][C:5]2[CH2:11][N:10]([CH2:12][C:13]#[N:14])[CH2:9][C:8](=[O:15])[N:7]([CH3:16])[C:6]=2[CH:17]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 24654Hydrazine hydrate (1:1)HCID 86633918HCID 86633918, compound

Product 1

HCID 86633917HCID 86633917, compoundYield 16.1%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To a mixture of (7-Methoxy-1-methyl-8-nitro-2-oxo-1,2,3,5-tetrahydro-benzo[e][1,4]diazepin-4-yl)-acetonitrile (0.47 g, 0.0016 mol) and Hydrazine hydrate (2.00 mL, 0.0411 mol) in Ethanol (10 mL, 0.2 mol) was added 10% Pd/C (10:90, Palladium:carbon black, 0.047 g) and reacted in an analogous manner to example 712. The reaction was filtered and evaporated. This product was chromatographed on SiO2 (13 g) with (20-1) DCM/MeOH giving (8-Amino-7-methoxy-1-methyl-2-oxo-1,2,3,5-tetrahydro-benzo[e][1,4]diazepin-4-yl)-acetonitrile as a tan solid (0.067 g, 16%). Mp 128-132° C.; LCMS (m/e)) 261 (M+1); 1H-NMR (DMSO, 400 MHz) δ 6.80 (s, 1H), 6.59 (s, 1H), 4.95 (s, 2H), 3.77 (s, 3H), 3.77-3.75 (d, 2H, J=9.35 Hz), 3.62 (s, 2H), 3.18 (s, 3H), 3.06 (s, 2H).

Workup

  1. customreacted in an analogous manner to example 712
  2. filtrationThe reaction was filtered
  3. customevaporated
  4. customThis product was chromatographed on SiO2 (13 g) with (20-1) DCM/MeOH

Sources & evidence

ORD record
ord-cd13320846d849249582f71f79b30849
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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