Diisopropylethylamine → HCID 131723016, compound

HRID 2269756Notes

Reaction equation

HRID 2269756 reaction equation
C1C(=O)N(OC(ON2C(=O)CCC2=O)=O)[C:3](=[O:4])C1.[CH2:19]([N:21]([CH:25](C)C)[CH:22](C)C)C.[NH2:28][C@H:29]([CH2:46][C:47]1[C:55]2[C:50](=[CH:51][CH:52]=[CH:53][CH:54]=2)[NH:49][CH:48]=1)[C:30]([N:32]1[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH2:35][CH:34](CN(C)C)[CH2:33]1)=[O:31].[Cl:56][C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][C:58]=1[N:63]1[CH2:68][CH2:67][NH:66][CH2:65][CH2:64]1.C(=O)([O-])O.[Na+]>C(#N)C>[Cl:56][C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][C:58]=1[N:63]1[CH2:68][CH2:67][N:66]([C:3]([NH:28][C@H:29]([CH:46]([CH2:19][N:21]([CH3:25])[CH3:22])[C:47]2[C:55]3[C:50](=[CH:51][CH:52]=[CH:53][CH:54]=3)[NH:49][CH:48]=2)[C:30]([N:32]2[C:41]3[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=3)[CH2:35][CH2:34][CH2:33]2)=[O:31])=[O:4])[CH2:65][CH2:64]1

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 4156281-(2-Chlorophenyl)piperazineHCID 516892Sodium BicarbonateHCID 676246Di(succinimido) carbonateHCID 10926917HCID 10926917, compound

Product 1

HCID 131723016HCID 131723016, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

N,N′-Disuccinimidyl carbonate (102 mg) and N-ethyldiisopropylamine (0.14 ml) were added to an acetonitrile (5 ml) solution of 1-[2-(R)-amino-3-(indol-3-yl)propanoyl]-3-(R,S)-(N,N-dimethylamino)methyl-1,2,3,4-tetrahydroquinoline (150 mg). The reaction mixture was stirred at room temperature for 30 minutes, to which were added an acetonitrile (1 ml) solution of 1-(2-chlorophenyl)piperazine (78 mg) and N-ethyldiusopropylamine (0.07 ml). The reaction mixture was stirred at room temperature for 2 hours. A saturated aqueous sodium hydrogencarbonate solution was added to the reaction mixture, which was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, then dried and concentrated. The residue was purified by alumina column chromatography (eluent: ethyl acetate/hexane=1/1 to 3/1) to obtain the entitled compound (158 mg) as an amorphous powder.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 2 hours
  2. extractionwas extracted with ethyl acetate
  3. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by alumina column chromatography (eluent: ethyl acetate/hexane=1/1 to 3/1)

Sources & evidence

ORD record
ord-77825082ecf34962bee6f32dfd7b6d25
Source dataset
uspto-grants-2001_12
Patent number
US06329389B1

Reaction notes

Loading…