Triethylamine → N-[(1R,2S)-1-[1-(4-fluorophenyl)indazol-5-yl]oxy-1-phenyl-propan-2-yl]propane-1-sulfonamide

HRID 1661446Notes

Reaction equation

HRID 1661446 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([O:17][C@H:18]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[C@@H:19]([NH2:21])[CH3:20])=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH2:35]([S:38](Cl)(=[O:40])=[O:39])[CH2:36][CH3:37]>C(#N)C.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([O:17][C@H:18]([C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=4)[C@@H:19]([NH:21][S:38]([CH2:35][CH2:36][CH3:37])(=[O:40])=[O:39])[CH3:20])=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 662791-Propanesulfonyl chlorideHCID 59339817(alphaS,betaR)-beta-{[1-(4-Fluorophenyl)-1H-indazole-5-yl]oxy}-alpha-methylbenzeneethanamine

Product 1

HCID 24953163N-[(1R,2S)-1-[1-(4-fluorophenyl)indazol-5-yl]oxy-1-phenyl-propan-2-yl]propane-1-sulfonamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of (1R,2S)-1-[1-(4-fluorophenyl)indazol-5-yl]oxy-1-phenyl-propan-2-amine (1a, 18 mg, 50 μmol) in acetonitrile (1 ml) was added triethylamine (100 μl), followed by propane-1-sulfonyl chloride (21 mg, 150 μmol). Stirring was continued overnight. The mixture was then diluted with water (300 μl), and the title compound isolated by preparative HPLC to afford 23 mg (83%) as white solid.

Sources & evidence

ORD record
ord-c7cb9fb788f84595ae298feea8769ed9
Source dataset
uspto-grants-2011_10
Patent number
US08030340B2

Reaction notes

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