Triethylamine → HCID 88258910, compound

HRID 1421901Notes

Reaction equation

HRID 1421901 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 44329321HCID 44329321, compound

Product 1

HCID 88258910HCID 88258910, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methanesulfonyl chloride (0.04 ml, 0.5 mmol) was added to a stirred solution of trans-7-hydroxy-4-(4-(4-phenylbenzoylamino)butyl)-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinoline(E3, 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 12 h and then poured onto saturated aqueous K2CO3 (10 ml) and extracted onto dichloromethane (3×10 ml). The combined extracts were washed with brine, dried (Na2SO4) and evaporated in vacuo to give an off-white solid. Chromatography on silica using 50-100% ethyl acetate /pentane as elution gradient, afforded the free base of the title compound (200 mg, 94%). 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 onto dichloromethane (3×10 ml)
  2. washThe combined extracts were washed with brine
  3. dry with materialdried (Na2SO4)
  4. customevaporated in vacuo
  5. customto give an off-white solid
  6. washChromatography on silica using 50-100% ethyl acetate /pentane as elution gradient

Sources & evidence

ORD record
ord-d63386781ccc4ef0bbe961af26e5c9c8
Source dataset
uspto-grants-2000_06
Patent number
US06080752

Reaction notes

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