Diisopropylethylamine → (R)-1-(4-Fluorophenyl)-6-[6-((R)-3-fluoropyrrolidin-1-yl)-pyridine-3-sulfonyl]-4a-methoxymethyl-4,4a,5,6,7,8-hexahydro-1H-1,2,6-triaza-cyclopenta[b]naphthalene

HRID 1907298Notes

Reaction equation

HRID 1907298 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:20][CH2:19][C:18]3[C@:13]([CH2:31][O:32][CH3:33])([CH2:14][C:15]4[CH:23]=[N:22][N:21]([C:24]5[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=5)[C:16]=4[CH:17]=3)[CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.Cl.[F:44][C@@H:45]1[CH2:49][CH2:48][NH:47][CH2:46]1>C(#N)C.C(OCC)(=O)C>[F:30][C:27]1[CH:28]=[CH:29][C:24]([N:21]2[C:16]3[CH:17]=[C:18]4[C@:13]([CH2:31][O:32][CH3:33])([CH2:14][C:15]=3[CH:23]=[N:22]2)[CH2:12][N:11]([S:8]([C:5]2[CH:6]=[N:7][C:2]([N:47]3[CH2:48][CH2:49][C@@H:45]([F:44])[CH2:46]3)=[CH:3][CH:4]=2)(=[O:10])=[O:9])[CH2:20][CH2:19]4)=[CH:25][CH:26]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 2759162(3R)-3-fluoropyrrolidine hydrochlorideHCID 86669986HCID 86669986, compound

Product 1

HCID 56849036(R)-1-(4-Fluorophenyl)-6-[6-((R)-3-fluoropyrrolidin-1-yl)-pyridine-3-sulfonyl]-4a-methoxymethyl-4,4a,5,6,7,8-hexahydro-1H-1,2,6-triaza-cyclopenta[b]naphthalene

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (R)-6-(6-chloropyridine-3-sulfonyl)-4a-methoxymethyl-1-(4-fluorophenyl)-4,4a,5,6,7,8-hexahydro-1H-1,2,6-triazacyclopenta[b]naphthalene (0.098 g), diisopropylethylamine (0.194 g) and (R)-3-fluoropyrrolidine hydrochloride in acetonitrile was heated at 130° C. in a microwave reactor for 45 minutes. The solution was diluted with ethyl acetate, washed with water followed by brine, dried over sodium sulfate, filtered and the filtrate concentrated under reduced pressure. The residue was purified by column chromatography on silica gel, eluting with ethyl acetate in cyclohexane (0 to 3:2 by volume), to afford the title compound as a white solid (0.089 g). LCMS (Method F): 542 (M+H)+, Retention time 5.0 minutes

Workup

  1. washwashed with water
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel
  6. washeluting with ethyl acetate in cyclohexane (0 to 3:2 by volume)

Sources & evidence

ORD record
ord-00e87988e3bc46b1a244bc55f9df8194
Source dataset
uspto-grants-2013_12
Patent number
US08598154B2

Reaction notes

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