Dimethylformamide → HCID 9979776, compound

HRID 1110208Notes

Reaction equation

HRID 1110208 reaction equation
[CH3:1][N:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[C:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:5][C@@H:4]([NH:19][C:20]([O:22]C2C=CC([N+]([O-])=O)=CC=2)=O)[C:3]1=[O:32].CN(C)C=O.[NH2:38][C:39]1[CH:40]=[C:41]2[C:45](=[CH:46][CH:47]=1)[CH2:44][CH2:43][CH2:42]2.C(N(CC)CC)C>O>[CH2:44]1[C:45]2[C:41](=[CH:40][C:39]([NH:38][C:20]([NH:19][C@@H:4]3[N:5]=[C:6]([C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=4)[C:7]4[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=4[N:2]([CH3:1])[C:3]3=[O:32])=[O:22])=[CH:47][CH:46]=2)[CH2:42][CH2:43]1

Participants

6

Reactant 4

HCID 6228Dimethylformamide2×HCID 8471TriethylamineHCID 90496Indan-5-amineHCID 9980117HCID 9980117, compound

Product 1

HCID 9979776HCID 9979776, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(R)-1,3-Dihydro-1-methyl-3-(p-nitrophenyloxycarbonyl)amino-5-phenyl-2H-1,4-benzodiazepin-2-one (200 mg. 0.46 mmole) was dissolved in 2 ml of freshly degassed, dry N,N-dimethylformamide (DMF) and treated with 1 ml of DMF containing 74 mg (0.50 mmole) of 5-aminoindane and 97.4 μl of triethylamine. The resulting solution was stirred under nitrogen for four hours. The reaction mixture was poured into 75 ml of water and extracted with ethyl acetate (3×40 ml). The combined organic extracts were washed with 1N sodium hydroxide solution (4×100 ml), 10% citric acid solution (2×100 ml), and brine. The organic extracts were then dried and the residue was plug-filtered through a six inch silica gel column. The eluate was concentrated and the residue was crystallized from a methylene chloride-ether mixture to give the title compound: mp 156°-158° C. NMR: Structure is consistent with the spectrum.

Workup

  1. customof freshly degassed
  2. extractionextracted with ethyl acetate (3×40 ml)
  3. washThe combined organic extracts were washed with 1N sodium hydroxide solution (4×100 ml), 10% citric acid solution (2×100 ml), and brine
  4. customThe organic extracts were then dried
  5. filtrationthe residue was plug-filtered through a six inch silica gel column
  6. concentrationThe eluate was concentrated
  7. customthe residue was crystallized from a methylene chloride-ether mixture

Sources & evidence

ORD record
ord-789f451c6666418e92e620bbc1a09a56
Source dataset
uspto-grants-1994_06
Patent number
US05324726

Reaction notes

Loading…