Triethylamine → HCID 86755479, compound

HRID 1421902Notes

Reaction equation

HRID 1421902 reaction equation
[CH3:1][S:2]([Cl:5])(=[O:4])=[O:3].[OH:6][C:7]1[C:20]2[CH2:19][CH2:18][C@H:17]3[C@H:12]([CH2:13][CH2:14][CH2:15][N:16]3[CH2:21][CH2:22][CH2:23][CH2:24][NH:25][C:26](=[O:39])[C:27]3[CH:32]=[CH:31][C:30]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)=[CH:29][CH:28]=3)[C:11]=2[CH:10]=[CH:9][CH:8]=1.C(N(CC)CC)C.C([O-])([O-])=O.[K+].[K+]>ClCCl>[ClH:5].[CH3:1][S:2]([O:6][C:7]1[C:20]2[CH2:19][CH2:18][C@H:17]3[C@H:12]([CH2:13][CH2:14][CH2:15][N:16]3[CH2:21][CH2:22][CH2:23][CH2:24][NH:25][C:26](=[O:39])[C:27]3[CH:32]=[CH:31][C:30]([C:33]4[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=4)=[CH:29][CH:28]=3)[C:11]=2[CH:10]=[CH:9][CH:8]=1)(=[O:4])=[O:3]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chlorideHCID 44533192HCID 44533192, compound

Product 1

HCID 86755479HCID 86755479, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methanesulfonyl chloride (0.04 ml, 0.5 mmol) was added to stirred solution of cis-7-hydroxy-4-(4-(4-phenylbenzoylamino)butyl)-1,2,3,4,4a,5 ,6,10b-octahydrobenzo[f]quinoline (E4, 200 mg, 0.4 mmol) and triethylamine (0.07 ml, 0.5 mmol) in dichloromethane (5 ml) at room temperature. The mixture was stirred for 2 h and then poured onto saturated aqueous K2CO3 (10 ml) and extracted into dichloromethane (3×10 ml). The combined organic extracts were washed with brine, dried (Na2SO4) and evaporated in vacuo to give a solid which was chromatographed on silica using 50-100% ethyl acetate/pentane as elution gradient to give the free base of the title compound (156 mg, 73%). The free base was treated with 1M ethereal HCl in dichloromethane to afford after evaporation the title compound as a colourless solid.

Workup

  1. extractionextracted into dichloromethane (3×10 ml)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried (Na2SO4)
  4. customevaporated in vacuo
  5. customto give a solid which
  6. customwas chromatographed on silica using 50-100% ethyl acetate/pentane as elution gradient

Sources & evidence

ORD record
ord-d737e92b10d54fe1aac37b03e8dafe7e
Source dataset
uspto-grants-2000_06
Patent number
US06080752

Reaction notes

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