HCID 10203569, compound → HCID 69460802, compound

HRID 1297129Notes

Reaction equation

HRID 1297129 reaction equation
[C:1]([C:3]1[CH:33]=[CH:32][CH:31]=[CH:30][C:4]=1[CH2:5][CH:6]1[N:12]=[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:10]2[CH:19]=[C:20]([O:25][CH3:26])[C:21]([O:23][CH3:24])=[CH:22][C:9]=2[N:8]([CH2:27][CH3:28])[C:7]1=[O:29])#[N:2]>[Ni].CO>[NH2:2][CH2:1][C:3]1[CH:33]=[CH:32][CH:31]=[CH:30][C:4]=1[CH2:5][CH:6]1[N:12]=[C:11]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:10]2[CH:19]=[C:20]([O:25][CH3:26])[C:21]([O:23][CH3:24])=[CH:22][C:9]=2[N:8]([CH2:27][CH3:28])[C:7]1=[O:29]

Participants

4

Reactant 1

HCID 10203569HCID 10203569, compound

Product 1

HCID 69460802HCID 69460802, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

Stir a mixture of 100 mg (0.23 mmol) of 3-(2-cyanobenzyl)-7,8-dimethoxy-1-ethyl-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one IIce, 10 mg of Raney nickel in 5 ml of MeOH under an H2 atmosphere at room temperature and pressure for 12 hours. Filter the suspension on celite, rinse three times with 10 ml of MeOH. Evaporate to dryness and purify by silica chromatography (AcOEt 5/CH2Cl2 4/EtOH 1, CH2Cl2 4/MeOH 1). Recrystallize in EtOH. Yield: 70%. M: 280° C. with degradation. 1H-NMR (CDCl3, 300 MHz): d 0.98–1.02 (m, 3H, CH3), 3.33–3.37 (m, 1H, 1H CHCH2), 3.54–3.59 (m, 5H, OCH3+1H NCH2CH3+1H CHCH2), 3.79–3.84 m, 1H, CHCH2), 3.89 (s, 3H, OCH3), 4.25–4.32 (m, 3H, CH2NH2+1H NCH2CH3), 6.40 (s, 1H Ar), 6.78 (s, 1H Ar), 7.02–7.63 (m, 10H Ar). Mass: (M+H)+=444.22

Workup

  1. filtrationFilter the suspension on celite
  2. washrinse three times with 10 ml of MeOH
  3. customEvaporate to dryness
  4. custompurify by silica chromatography (AcOEt 5/CH2Cl2 4/EtOH 1, CH2Cl2 4/MeOH 1)
  5. customRecrystallize in EtOH
  6. custom280° C.

Sources & evidence

ORD record
ord-2c512a65238f4d7fa5fd560e4d16f7e7
Source dataset
uspto-grants-2007_07
Patent number
US07250410B2

Reaction notes

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