Dimethylformamide → HCID 67264619, compound

HRID 1041070Notes

Reaction equation

HRID 1041070 reaction equation
[CH3:1][S:2]([N:5]1[CH2:11][C:10]2[C:12]([N+:18]([O-])=O)=[C:13]([O:16][CH3:17])[CH:14]=[CH:15][C:9]=2[NH:8][C:7](=[O:21])[CH2:6]1)(=[O:4])=[O:3].CN(C)C=O>>[NH2:18][C:12]1[C:10]2[CH2:11][N:5]([S:2]([CH3:1])(=[O:4])=[O:3])[CH2:6][C:7](=[O:21])[NH:8][C:9]=2[CH:15]=[CH:14][C:13]=1[O:16][CH3:17]

Participants

3

Reactant 2

HCID 6228DimethylformamideHCID 67263925HCID 67263925, compound

Product 1

HCID 67264619HCID 67264619, compoundYield 97.4%

Procedure

4-Methanesulfonyl-7-methoxy-6-nitro-1,3,4,5-tetrahydro-benzo[e][1,4]diazepin-2-one (0.57 g, 0.0018 mol) was hydrogenated in N,N-Dimethylformamide (40 mL, 0.5 mol) 10% Pd/C (10:90, Palladium:carbon black, 0.057 g) for 5 days. After the reaction was filtered and the filtrate evaporated. the residue was triturated with ether giving 6-Amino-4-methanesulfonyl-7-methoxy-1,3,4,5-tetrahydro-benzo[e][1,4]diazepin-2-one as a grey solid (0.50 g, 97%). Mp 232-233° C.; LCMS (m/e) 285 (M); 1H-NMR (DMSO, 400 MHz) δ 1H-NMR (DMSO, 400 MHz) δ 9.93 (s, 1H), 6.84-6.82 (d, 1H, J=8.59 Hz), 6.38-6.36 (d, 2H, J=8.33 Hz), 4.85 (s, 2H), 4.35 (s, 2H), 3.77 (s, 3H), 3.68 (s, 2H), 2.98 (s, 3H).

Workup

  1. filtrationAfter the reaction was filtered
  2. customthe filtrate evaporated
  3. customthe residue was triturated with ether

Sources & evidence

ORD record
ord-65c33973e03e4005ab3193dccf94c14d
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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