Triethylamine → 4-(4-((R)-2-(1H-Indol-1-yl)propanoyl)-3-methylpiperazin-1-yl)-N-(thiazol-2-yl)benzenesulfonamide

HRID 1715896Notes

Reaction equation

HRID 1715896 reaction equation
[CH3:1][CH:2]1[NH:7][CH2:6][CH2:5][N:4]([C:8]2[CH:13]=[CH:12][C:11]([S:14]([NH:17][C:18]3[S:19][CH:20]=[CH:21][N:22]=3)(=[O:16])=[O:15])=[CH:10][CH:9]=2)[CH2:3]1.F[C:24]1[CH:25]=[C:26]2[C:30](=[CH:31][CH:32]=1)[N:29]([CH2:33][C:34]([OH:36])=O)[CH:28]=[CH:27]2.[CH3:37]N([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>O.CC#N.CN(C=O)C>[N:29]1([C@H:33]([CH3:37])[C:34]([N:7]2[CH2:6][CH2:5][N:4]([C:8]3[CH:13]=[CH:12][C:11]([S:14]([NH:17][C:18]4[S:19][CH:20]=[CH:21][N:22]=4)(=[O:15])=[O:16])=[CH:10][CH:9]=3)[CH2:3][CH:2]2[CH3:1])=[O:36])[C:30]2[C:26](=[CH:25][CH:24]=[CH:32][CH:31]=2)[CH:27]=[CH:28]1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 45036900(5-Fluoroindol-1-yl)acetic acidHCID 594661204-(3-methylpiperazin-1-yl)-N-(thiazol-2-yl)benzenesulfonamide

Product 1

HCID 536276084-(4-((R)-2-(1H-Indol-1-yl)propanoyl)-3-methylpiperazin-1-yl)-N-(thiazol-2-yl)benzenesulfonamide

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

Synthesized according to general procedure 9, method A. The reaction was set up with 0.1 mmol 4-(3-methylpiperazin-1-yl)-N-(thiazol-2-yl)benzenesulfonamide, 0.1 μmol 2-(5-fluoro-1H-indol-1-yl)acetic acid, 0.1 μmol BOP reagent, 0.1 mmol triethylamine and DMF (300 μL). LC/MS (100%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)), m/z: M+1 obs=510.4; tR=3.08 min.

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-b711dfedcec6412ea8d4a2bf0d0fd46c
Source dataset
uspto-grants-2010_09
Patent number
US07799822B2

Reaction notes

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