Dichloromethane → 7,8-dimethoxy-1-methyl-5-(2-phenylethyl)-1,3-dihydro-2H-1,4-benzodiazepin-2-one

HRID 1297101Notes

Reaction equation

HRID 1297101 reaction equation
[CH3:1][O:2][C:3]1[C:4]([O:24][CH3:25])=[CH:5][C:6]2[N:12]([CH3:13])[C:11](=[O:14])[CH2:10][N:9]=[C:8]([C:15]#[C:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:7]=2[CH:23]=1.C(Cl)Cl>CO.[Pd]>[CH3:1][O:2][C:3]1[C:4]([O:24][CH3:25])=[CH:5][C:6]2[N:12]([CH3:13])[C:11](=[O:14])[CH2:10][N:9]=[C:8]([CH2:15][CH2:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:7]=2[CH:23]=1

Participants

5

Reactant 2

HCID 6344DichloromethaneHCID 573973617,8-Dimethoxy-1-methyl-5-(2-phenylethynyl)-1,3-dihydro-1,4-benzodiazepin-2-one

Product 1

HCID 99458027,8-dimethoxy-1-methyl-5-(2-phenylethyl)-1,3-dihydro-2H-1,4-benzodiazepin-2-oneYield 5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Stir a mixture of 80 mg (0.24 mmol) of 7,8-dimethoxy-1-methyl-5-(2-phenylethynyl)-1,3-dihydro-1,4-benzodiazepin-2-one 132, 15 mg of 10% Pd/C by weight in 5 ml of MeOH and 5 ml of CH2Cl2 under 70 psi of H2 for 48 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 1, then AcOEt). Yield: 5%. M: 112–115° C. 1H-NMR (CDCl3, 300 MHz): d 2.95–3.07 (m, 4H, CH2CH2), 3.28 (s, 3H, NCH3), 3.87 (s, 3H, OCH3), 3.93 (s, 3H, OCH3), 4.10 (AB system, ? d=0.96, JAB=10.2, 2H, CH2), 6.67 (s, 1H Ar), 6.78 (s, 1H Ar), 7.15–7.25 (m, 5H Ar). Mass: (M+H)+=339.15

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 1
  5. custom112–115° C

Sources & evidence

ORD record
ord-840ffd72c84b4141bc21d96edcb2874c
Source dataset
uspto-grants-2007_07
Patent number
US07250410B2

Reaction notes

Loading…