HCID 57853849, compound → HCID 67263433, compound

HRID 1687937Notes

Reaction equation

HRID 1687937 reaction equation
[CH2:1]([N:8]1[CH2:14][C:13]2[CH:15]=[C:16]([O:22][CH3:23])[C:17]([N+:19]([O-])=O)=[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]>[NH2:19][C:17]1[C:16]([O:22][CH3:23])=[CH:15][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]=1

Participants

4

Reactant 1

HCID 57853849HCID 57853849, compound

Product 1

HCID 67263433HCID 67263433, compoundYield 97.4%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A solution of 4-benzyl-7-methoxy-8-nitro-1,3,4,5-tetrahydro-benzo[e][1,4]diazepin-2-one (125 mg, 0.38 mmol) in methanol (25 mL) was treated with Ra—Ni (˜100 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 8-amino-4-benzyl-7-methoxy-1,3,4,5-tetrahydro-benzo[e][1,4]diazepin-2-one (110 mg, 97%) as a mustard yellow solid; 1H NMR (400 MHz, DMSO-d6) δ 9.61 (s, 1H), 7.34 (m, 5H), 6.66 (s, 1H), 6.33 (s, 1H), 4.84 (s, 2H), 3.74 (s, 3H), 3.65 (s, 2H), 3.49 (s, 2H), 2.98 (s, 2H); MS (m/e) 298 (M+1); mp 135° C. (dec.).

Workup

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

Sources & evidence

ORD record
ord-2398e6b3bc7e42d7bcbd3dff8350bb62
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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