Acetonitrile → HCID 11511843, compound

HRID 1713030Notes

Reaction equation

HRID 1713030 reaction equation
C(OC(=O)C(CC)CCN1C(=S)[N:11]2[C:12]3[CH:13]=[C:14]([C:18]4[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=4)[O:15][C:16]=3[CH:17]=[C:10]2[C:9]1=[O:27])C.[CH2:31]([N:33]([CH2:47][CH3:48])[C:34](=[O:46])[CH2:35][C:36]1([CH2:42][N:43]=[C:44]=[S:45])[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]1)[CH3:32].C([O-])([O-])=O.[K+].[K+].C(#N)C>C(Cl)(Cl)Cl.O>[CH2:34]([O:46][C:9]([C:10]1[NH:11][C:12]2[CH:13]=[C:14]([C:18]3[CH:19]=[CH:20][C:21]([Cl:24])=[CH:22][CH:23]=3)[O:15][C:16]=2[CH:17]=1)=[O:27])[CH3:35].[Cl:24][C:21]1[CH:20]=[CH:19][C:18]([C:14]2[O:15][C:16]3[CH:17]=[C:10]4[C:9](=[O:27])[N:43]([CH2:42][C:36]5([CH2:35][C:34]([N:33]([CH2:31][CH3:32])[CH2:47][CH3:48])=[O:46])[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41]5)[C:44](=[S:45])[N:11]4[C:12]=3[CH:13]=2)=[CH:23][CH:22]=1

Participants

8

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 86618329HCID 86618329, compoundHCID 86618332HCID 86618332, compound

Product 2

HCID 11511843HCID 11511843, compoundYield 20%HCID 12527106HCID 12527106, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Conditions

Temperature
120 °C

Procedure

2-(4-Chloro-phenyl)-4H-furo[3,2-b]pyrrole-5-carboxylic acid ethyl ester (15 mg, 0.05 mmol) was prepared as described hereinabove (see, preparation of Compound 4), and placed in a heavy-walled glass tube with a threaded Teflon plug. N,N-diethyl-2-(1-isothiocyanatomethyl-cyclohexyl)-acetamide (84 mg, 0.2 mmol, 4 molequivalents) and K2CO3 (10 mg, 0.07 mmol, 1.4 molequivalents) were added thereto, the glass tube was sealed and the mixture was heated while stirring at 120° C. for 6 hours. The mixture was then dissolved in chloroform, washed with water, dried over Na2SO4 and the solvent was evaporated under reduced pressure. The purified product was isolated by HPLC, using an acetonitrile:water gradient as eluent, to give Compound 24 (5.16 mg, 20% yield) as an orange solid.

Workup

  1. customthe glass tube was sealed
  2. temperaturethe mixture was heated
  3. washwashed with water
  4. dry with materialdried over Na2SO4
  5. customthe solvent was evaporated under reduced pressure
  6. customThe purified product was isolated by HPLC

Sources & evidence

ORD record
ord-3df4ec9dc80c4a62889b1766f7783aa0
Source dataset
uspto-grants-2010_09
Patent number
US07795255B2

Reaction notes

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