Ammonia → HCID 10138332, compound

HRID 1297132Notes

Reaction equation

HRID 1297132 reaction equation
[CH2:1]([N:3]1[C:9]2[CH:10]=[C:11]([O:16][CH3:17])[C:12]([O:14][CH3:15])=[CH:13][C:8]=2[C:7]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[N:6][CH:5]([CH2:24][C:25]2[CH:26]=[C:27]([CH:30]=[CH:31][CH:32]=2)[C:28]#[N:29])[C:4]1=[O:33])[CH3:2].N>[Ni].CO>[NH2:29][CH2:28][C:27]1[CH:26]=[C:25]([CH:32]=[CH:31][CH:30]=1)[CH2:24][CH:5]1[N:6]=[C:7]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:8]2[CH:13]=[C:12]([O:14][CH3:15])[C:11]([O:16][CH3:17])=[CH:10][C:9]=2[N:3]([CH2:1][CH3:2])[C:4]1=[O:33]

Participants

5

Reactant 2

HCID 222AmmoniaHCID 69461612HCID 69461612, compound

Product 1

HCID 10138332HCID 10138332, compoundYield 99.1%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

Leave under hydrogen pressure (Patm) for 12 hours, 40 mg of 3-[(1-ethyl-7,8-dimethoxy-2-oxo-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-3-yl)methyl]benzonitrile (IIcp), 0.4 ml of 30% ammonia, 4 ml of methanol, 1 spatula tip of Raney nickel. Filter on celite, rinse several times with methanol. Evaporate to dryness. Take up in 50 ml of dichloromethane, wash three times with 50 ml of 0.5 M NH3 and twice with water. Dry the organic phase on Na2SO4. Evaporate to dryness. Recrystallize in ether. Filter. One obtains 40 mg of the abovenamed product in the form of a white powder. Yield: 55%. M: 122–125° C. 1H-NMR (CDCl3, 200 MHz): d 1.10 (s, 3H, CH3), 1.30 (m, 2H exchangeable —NH2), 3.50–3.89 (m, 8H, 1H —CH2Ph+1H —NCH2+CH+CH2—NH2+OCH3), 3.98–4.11 (m, 4H, 1H —CH2Ph+OCH3), 4.37–4.47 (m, 1H —NCH2), 6.67 (s, 1H Ar), 6.84 (s,1H Ar), 7.20–7.64 (m, 9H Ar).

Workup

  1. customLeave under hydrogen pressure (Patm) for 12 hours
  2. filtrationFilter on celite
  3. washrinse several times with methanol
  4. customEvaporate to dryness
  5. washwash three times with 50 ml of 0.5 M NH3
  6. customDry the organic phase on Na2SO4
  7. customEvaporate to dryness
  8. customRecrystallize in ether
  9. filtrationFilter

Sources & evidence

ORD record
ord-3660ef13082d42b589ef18b4bafa37e7
Source dataset
uspto-grants-2007_07
Patent number
US07250410B2

Reaction notes

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