Triethylamine → 4-(4-(3-(5-Chloro-1H-indol-1-yl)propanoyl)piperazin-1-yl)-N-(pyrimidin-4-yl)benzenesulfonamide

HRID 1876643Notes

Reaction equation

HRID 1876643 reaction equation
[N:1]1([C:7]2[CH:12]=[CH:11][C:10]([S:13]([NH:16][C:17]3[CH:22]=[CH:21][N:20]=[CH:19][N:18]=3)(=[O:15])=[O:14])=[CH:9][CH:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[Cl:23][C:24]1[CH:25]=[C:26]2[C:30](=[CH:31][CH:32]=1)[N:29]([CH2:33][CH2:34][C:35](O)=[O:36])[CH:28]=[CH:27]2.CN([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>[Cl:23][C:24]1[CH:25]=[C:26]2[C:30](=[CH:31][CH:32]=1)[N:29]([CH2:33][CH2:34][C:35]([N:4]1[CH2:3][CH2:2][N:1]([C:7]3[CH:12]=[CH:11][C:10]([S:13]([NH:16][C:17]4[CH:22]=[CH:21][N:20]=[CH:19][N:18]=4)(=[O:14])=[O:15])=[CH:9][CH:8]=3)[CH2:6][CH2:5]1)=[O:36])[CH:28]=[CH:27]2

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 594656354-(piperazin-1-yl)-N-(pyrimidin-4-yl)benzenesulfonamideHCID 594664433-(5-chloro-1H-indol-1-yl)propanoic acid

Product 1

HCID 536275984-(4-(3-(5-Chloro-1H-indol-1-yl)propanoyl)piperazin-1-yl)-N-(pyrimidin-4-yl)benzenesulfonamide

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

Synthesized according to general procedure 5, method A. The reaction was set up with 0.11 mmol 4-(piperazin-1-yl)-N-(pyrimidin-4-yl)benzenesulfonamide, 0.17 mmol 3-(5-chloro-1H-indol-1-yl)propanoic acid, 0.17 mmol BOP reagent, 0.17 mmol triethylamine and 300 μL DMF. LC/MS (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)), m/z: M+1 obs=525.2; tR=2.87 min.

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-84698175f73145599647da3ac88d4432
Source dataset
uspto-grants-2012_11
Patent number
US08309587B2

Reaction notes

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