HCID 69461264, compound → HCID 69463018, compound

HRID 1297127Notes

Reaction equation

HRID 1297127 reaction equation
[CH3:1][O:2][C:3]1[C:4]([O:33][CH3:34])=[CH:5][C:6]2[N:12]([CH2:13][CH3:14])[C:11](=[O:15])[CH:10]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[N+:23]([O-])=O)[N:9]=[C:8]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:7]=2[CH:32]=1>CO.[Pd]>[CH3:1][O:2][C:3]1[C:4]([O:33][CH3:34])=[CH:5][C:6]2[N:12]([CH2:13][CH3:14])[C:11](=[O:15])[CH:10]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[NH2:23])[N:9]=[C:8]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:7]=2[CH:32]=1

Participants

4

Reactant 1

HCID 69461264HCID 69461264, compound

Product 1

HCID 69463018HCID 69463018, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Stir a mixture of 80 mg (0.17 mmol) of 7,8-dimethoxy-1-ethyl-3-(2-nitrobenzyl)-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one IIbh, 10 mg of Pd/C 10% by weight in 15 ml of MeOH under 65 psi of H2 at room temperature for 2 hours. Filter the suspension on celite, rinse three times with 10 ml of MeOH. Evaporate to dryness and purify by silica chromatography (AcOEt 1/hexane 4, 1/2). Recrystallize in EtOH. Yield: 70%. M: degradation at 280° C. 1H-NMR (DMSO, 300 MHz): d 0.86–0.90 (m, 3H, CH3), 3.21–3.31 (m, 2H, CHCH2), 3.59 (s, 3H, OCH3), 3.69–3.76(m, 2H, NCH+CHCH2), 3.88 (s, 3H, OCH3), 4.22–4.30 (m, 1H, NCH), 6.46–6.51 (m, 1H Ar), 6.59–6.61 (m, 2H Ar), 6.85–6.88 (m, 1H Ar), 7.01–7.03 (m, 1H Ar), 7.41–7.53 (m, 5H Ar). Mass: (M+H)+=430.22.

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 1/hexane 4, 1/2)
  5. customRecrystallize in EtOH
  6. customat 280° C

Sources & evidence

ORD record
ord-3e8b5fd120d44079b2e3cbf052df91ee
Source dataset
uspto-grants-2007_07
Patent number
US07250410B2

Reaction notes

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