HCID 57853839, compound → HCID 67264415, compound

HRID 1687939Notes

Reaction equation

HRID 1687939 reaction equation
[CH2:1]([N:8]1[CH2:14][C:13]2[C:15]([N+:21]([O-])=O)=[C:16]([O:19][CH3:20])[CH:17]=[CH:18][C:12]=2[NH:11][C:10](=[O:24])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO.[Ni]>[NH2:21][C:15]1[C:13]2[CH2:14][N:8]([CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH2:9][C:10](=[O:24])[NH:11][C:12]=2[CH:18]=[CH:17][C:16]=1[O:19][CH3:20]

Participants

4

Reactant 1

HCID 57853839HCID 57853839, compound

Product 1

HCID 67264415HCID 67264415, compoundYield 98.8%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A solution of 4-benzyl-7-methoxy-6-nitro-1,3,4,5-tetrahydro-benzo[e][1,4]diazepin-2-one (860 mg, 2.6 mmol) in methanol (100 mL) was treated with Ra—Ni (˜200 mg; 2800 grade) and shaken on a Paar apparatus under 40 psi H2. After one hour LCMS showed completion of the reaction. The mixture was filtered and concentrated to constant weight to afford 6-amino-4-benzyl-7-methoxy-1,3,4,5-tetrahydro-benzo[e][1,4]diazepin-2-one (764 mg, 98%) as a tan solid; 1H NMR (400 MHz, DMSO-d6) δ 9.62 (s, 1H), 7.34 (m, 5H), 6.75 (d, J=8 Hz, 1H), 6.27 (d, J=8 Hz, 1H), 4.74 (s, 2H), 3.77 (s, 3H), 3.72 (s, 2H), 3.69 (s, 2H), 2.85 (s, 2H); MS (m/e) 298 (M+1); mp 153° C. (dec.).

Workup

  1. customcompletion of the reaction
  2. filtrationThe mixture was filtered
  3. concentrationconcentrated to constant weight

Sources & evidence

ORD record
ord-a1e42c9d3a2b4b07ae2ca98f8541a1e1
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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