Ethanol → HCID 67264014, compound

HRID 1041064Notes

Reaction equation

HRID 1041064 reaction equation
[CH:1]1([CH2:4][N:5]2[CH2:11][C:10]3[CH:12]=[C:13]([O:19][CH3:20])[C:14]([N+:16]([O-])=O)=[CH:15][C:9]=3[N:8]([CH3:21])[C:7](=[O:22])[CH2:6]2)[CH2:3][CH2:2]1.C(O)C.C(OCC)(=O)C>[Pd]>[NH2:16][C:14]1[C:13]([O:19][CH3:20])=[CH:12][C:10]2[CH2:11][N:5]([CH2:4][CH:1]3[CH2:2][CH2:3]3)[CH2:6][C:7](=[O:22])[N:8]([CH3:21])[C:9]=2[CH:15]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 8857Ethyl AcetateHCID 67264467HCID 67264467, compound

Product 1

HCID 67264014HCID 67264014, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

4-Cyclopropylmethyl-7-methoxy-1-methyl-8-nitro-1,3,4,5-tetrahydro-benzo[e][1,4]diazepin-2-one (0.5 g, 0.002 mol) was hydrogenated in Ethanol (40 mL, 0.7 mol) and Ethyl acetate (40 mL, 0.4 mol) with 10% Pd/C (10:90, Palladium:carbon black, 0.082 g) in an analogous manner to example N26-F to give 8-Amino-4-cyclopropylmethyl-7-methoxy-1-methyl-1,3,4,5-tetrahydro-benzo[e][1,4]diazepin-2-one as an oil (0.43 g, 90%). LCMS (m/e) 276 (M+1); 1H-NMR (DMSO, 400 MHz) δ 6.76 (s, 1H), 6.57 (s, 1H), 4.88 (s, 2H), 3.77 (s, 3H), 3.44 (s, 2H), 3.05 (s, 3H), 2.89 (s, 2H), 2.38-2.37 (d, 2H, J=15.41 Hz), 1.26-1.24 (m, 1H), 0.85-0.75 (m, 2H), 0.49-0.47 (d, 2H, J=7.83 Hz), 0.16-0.15 (d, 2H, J=4.80 Hz).

Sources & evidence

ORD record
ord-af07711b842a47199528ae87ef5c438f
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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