Triethylamine → HCID 11717733, compound

HRID 1713036Notes

Reaction equation

HRID 1713036 reaction equation
C(OC(=O)C(CC)[CH2:6][CH2:7][N:8]1[C:25](=[S:26])[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.N(C[CH2:35][CH2:36][O:37][CH3:38])=C=S.C(N(CC)CC)C>C(Cl)(Cl)Cl.C(OCC)(=O)C>[CH2:36]([O:37][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:22]=[CH:23][C:18]([C:14]2[O:15][C:16]3[CH:17]=[C:10]4[C:9](=[O:27])[N:8]([CH2:7][CH2:6][CH2:36][O:37][CH3:38])[C:25](=[S:26])[N:11]4[C:12]=3[CH:13]=2)=[CH:19][CH:20]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 1402743-Methoxypropyl isothiocyanateHCID 86618329HCID 86618329, compound

Product 2

HCID 11717733HCID 11717733, compoundYield 35%HCID 12527106HCID 12527106, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

2-(4-Chloro-phenyl)-4H-furo[3,2-b]pyrrole-5-carboxylic acid ethyl ester (29 mg, 0.1 mmol) was prepared as described hereinabove (see, preparation of Compound 4), and placed in a heavy-walled glass tube with a threaded Teflon plug. 1-Isothiocyanato-3-methoxy-propane (131 mg, 1. mmol, 10 molequivalents) and triethylamine (202 mg, 2 mmol, 20 molequivalents) were added thereto, the tube was sealed and the mixture was heated while stirring at 120° C. for 6 hours. The mixture was then cooled to room temperature, dissolved in chloroform and the solvents were evaporated under reduced pressure. The crude residue was dissolved in dichloromethane and was purified by column chromatography using a 95:5 hexane:ethyl acetate mixture as eluent, to give Compound 28 (13 mg, 35% yield) as an orange solid.

Workup

  1. customthe tube was sealed
  2. temperaturethe mixture was heated
  3. temperatureThe mixture was then cooled to room temperature
  4. customthe solvents were evaporated under reduced pressure
  5. dissolutionThe crude residue was dissolved in dichloromethane
  6. customwas purified by column chromatography

Sources & evidence

ORD record
ord-a8b3e3cab6054b598b2eb699662fb6f3
Source dataset
uspto-grants-2010_09
Patent number
US07795255B2

Reaction notes

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