Potassium Carbonate → HCID 57168868, compound

HRID 365342Notes

Reaction equation

HRID 365342 reaction equation
[CH:1]([O:4][C:5]([C:7]1[N:8]=[CH:9][C:10]2[NH:11][C:12]3[C:17]([C:18]=2[C:19]=1[CH2:20][CH3:21])=[CH:16][C:15](N)=[CH:14][CH:13]=3)=[O:6])([CH3:3])[CH3:2].[S-:23][C:24]#[N:25].[NH4+:26].C([O-])([O-])=O.[K+].[K+]>C(O)(=O)C.C(OCC)(=O)C.O>[CH:1]([O:4][C:5]([C:7]1[N:8]=[CH:9][C:10]2[NH:11][C:12]3[C:17]([C:18]=2[C:19]=1[CH2:20][CH3:21])=[C:16]1[N:25]=[C:24]([NH2:26])[S:23][C:15]1=[CH:14][CH:13]=3)=[O:6])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 15666Ammonium thiocyanateHCID 53846183HCID 53846183, compound

Product 1

HCID 57168868HCID 57168868, compoundYield 60.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 22728543Water ethylacetateSolvent

Procedure

297 mg of 6-amino-4-ethyl-β-carboline-3-carboxylic acid isopropyl ester is dissolved in 5 ml of acetic acid, mixed with 152 mg of ammonium thiocyanate and stirred for 1 hour at room temperature. Then, the reaction solution is cooled to 10° C. and mixed drop by drop with 0.05 ml of acetic bromine solution (0.5 ml of BR2 in 9.5 ml of acetic acid). It is stirred for 1 more hour at 10° C. and then heated to room temperature. The reaction mixture is taken up in ethyl acetate/water and neutralized with 10% K2CO3 solution. The organic phase is separated, dried and evaporated to dryness. The residue is triturated with ether. 214 mg of the title compound with a melting point of 160° C. (decomposition) is obtained.

Workup

  1. temperatureThen, the reaction solution is cooled to 10° C.
  2. stirringIt is stirred for 1 more hour at 10° C.
  3. temperatureheated to room temperature
  4. customThe organic phase is separated
  5. customdried
  6. customevaporated to dryness
  7. customThe residue is triturated with ether

Sources & evidence

ORD record
ord-9ddd7e339fdd4555a669257d87f8198f
Source dataset
uspto-grants-2000_10
Patent number
US06127368

Reaction notes

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