Triethylamine → (S)-4-(4-(2-(6-Chloro-3,4-dihydroquinolin-1(2H)-yl)acetyl)-3-methylpiperazin-1-yl)-N-(pyrimidin-4-yl)benzenesulfonamide

HRID 1715902Notes

Reaction equation

HRID 1715902 reaction equation
[CH3:1][C@@H: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[CH:23]=[CH:22][N:21]=[CH:20][N:19]=3)(=[O:16])=[O:15])=[CH:10][CH:9]=2)[CH2:3]1.[Cl:24][C:25]1[CH:26]=[C:27]2[C:32](=[CH:33][CH:34]=1)[N:31]([CH2:35][C:36](O)=[O:37])[CH2:30][CH2:29][CH2:28]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:24][C:25]1[CH:26]=[C:27]2[C:32](=[CH:33][CH:34]=1)[N:31]([CH2:35][C:36]([N:7]1[CH2:6][CH2:5][N:4]([C:8]3[CH:9]=[CH:10][C:11]([S:14]([NH:17][C:18]4[CH:23]=[CH:22][N:21]=[CH:20][N:19]=4)(=[O:16])=[O:15])=[CH:12][CH:13]=3)[CH2:3][C@@H:2]1[CH3:1])=[O:37])[CH2:30][CH2:29][CH2:28]2

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 59466223(S)-4-(3-methylpiperazin-1-yl)-N-(pyrimidin-4-yl)benzenesulfonamideHCID 670828012-(6-chloro-3,4-dihydroquinolin-1(2H)-yl)acetic acid

Product 1

HCID 59466345(S)-4-(4-(2-(6-Chloro-3,4-dihydroquinolin-1(2H)-yl)acetyl)-3-methylpiperazin-1-yl)-N-(pyrimidin-4-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 (S)-4-(3-methylpiperazin-1-yl)-N-(pyrimidin-4-yl)benzenesulfonamide, 0.15 mmol 2-(6-chloro-3,4-dihydroquinolin-1(2H)-yl)acetic acid, 0.15 mmol BOP reagent, 0.15 mmol triethylamine and DMF (300 μL). LC/MS (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)), m/z: M+1 obs=541.5; tR=2.96 min.

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-0932bfdeb1254fe581dc833085687a23
Source dataset
uspto-grants-2010_09
Patent number
US07799822B2

Reaction notes

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