HCID 69459234, compound → HCID 10159654, compound

HRID 1297125Notes

Reaction equation

HRID 1297125 reaction equation
[C:1]1(C2C=CC=CC=2)[CH:6]=[CH:5][C:4]([C:7]2[C:13]3[CH:14]=[C:15]([O:20][CH3:21])[C:16]([O:18][CH3:19])=[CH:17][C:12]=3[N:11]([CH2:22][CH3:23])[C:10](=[O:24])[CH2:9][N:8]=2)=[CH:3][CH:2]=1>[Pd].CO.C(Cl)Cl>[CH2:22]([N:11]1[C:12]2[CH:17]=[C:16]([O:18][CH3:19])[C:15]([O:20][CH3:21])=[CH:14][C:13]=2[C:7]([C:4]2[CH:3]=[CH:2][C:1]([CH2:13][CH2:7][C:4]3[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=3)=[CH:6][CH:5]=2)=[N:8][CH2:9][C:10]1=[O:24])[CH3:23]

Participants

5

Reactant 1

HCID 69459234HCID 69459234, compound

Product 1

HCID 10159654HCID 10159654, compoundYield 65.4%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Leave the following under hydrogen pressure (Patm) for 48 hours: 80 mg of 5-(1,1′-biphenyl-4-yl)-1-ethyl-7,8-dimethoxy-1,3-dihydro-2H-1,4-benzodiazepin-2-one (IIbp), 16 mg of 10% palladium on charcoal (20% by weight of product to reduce), in 30 ml of methanol and 1 ml of CH2Cl2. Filter on celite, rinse several times with methanol. Evaporate to dryness. Purify by silica chromatography (AcOEt 1/hexane 1). Recrystallize in ether. One obtains 28 mg of the abovenamed product in the form of a white powder. Yield: 35%. M: 148–150° C. 1H-NMR (CDCl3, 200 MHz): d 1.27 (t, 3H, —CH3), 3.00 (s, 4H, 2×—CH2). 3,37–3,40 (m, 2H, CH2), 3.45–3.65 (m, 4H, —OCH3+1H NCH2), 3.92 (s, 3H, OCH3), 4.21–4.48 (m, 1H, NCH2), 6.22 (d, 1H Ar), 6.77 (d, 1H Ar), 7.19–7.39 (m, 9H Ar).

Workup

  1. filtrationFilter on celite
  2. washrinse several times with methanol
  3. customEvaporate to dryness
  4. customPurify by silica chromatography (AcOEt 1/hexane 1)
  5. customRecrystallize in ether

Sources & evidence

ORD record
ord-8532fe370225422ab8da189231380fb2
Source dataset
uspto-grants-2007_07
Patent number
US07250410B2

Reaction notes

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