4-Toluenesulfonyl chloride → (S)-2-(4-isopropyl-2-oxo-3-(3-(4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)imidazolidin-1-yl)ethyl 4-methylbenzenesulfonate

HRID 539035Notes

Reaction equation

HRID 539035 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[CH2:8][C@H:7]([CH:9]([CH3:11])[CH3:10])[N:6]([C:12]2[CH:17]=[CH:16][N:15]3[N:18]=[CH:19][C:20]([C:21]4[CH:26]=[CH:25][C:24]([C:27]5[N:31]=[CH:30][N:29]([CH2:32][O:33][CH2:34][CH2:35][Si:36]([CH3:39])([CH3:38])[CH3:37])[N:28]=5)=[CH:23][CH:22]=4)=[C:14]3[N:13]=2)[C:5]1=[O:40].[CH3:41][C:42]1[CH:47]=[CH:46][C:45]([S:48](Cl)(=[O:50])=[O:49])=[CH:44][CH:43]=1>N1C=CC=CC=1>[CH3:41][C:42]1[CH:47]=[CH:46][C:45]([S:48]([O:1][CH2:2][CH2:3][N:4]2[CH2:8][C@H:7]([CH:9]([CH3:11])[CH3:10])[N:6]([C:12]3[CH:17]=[CH:16][N:15]4[N:18]=[CH:19][C:20]([C:21]5[CH:22]=[CH:23][C:24]([C:27]6[N:31]=[CH:30][N:29]([CH2:32][O:33][CH2:34][CH2:35][Si:36]([CH3:37])([CH3:39])[CH3:38])[N:28]=6)=[CH:25][CH:26]=5)=[C:14]4[N:13]=3)[C:5]2=[O:40])(=[O:50])=[O:49])=[CH:44][CH:43]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 67034260(S)-1-(2-hydroxyethyl)-4-isopropyl-3-(3-(4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)imidazolidin-2-one

Product 1

HCID 86667826(S)-2-(4-isopropyl-2-oxo-3-(3-(4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)imidazolidin-1-yl)ethyl 4-methylbenzenesulfonateYield 68.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of (S)-1-(2-hydroxyethyl)-4-isopropyl-3-(3-(4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)imidazolidin-2-one (Example 25, Step 6; 0.160 g, 0.284 mmol) in pyridine was added 4-methylbenzene-1-sulfonyl chloride (0.136 g, 0.711 mmol) and the reaction stirred overnight at ambient temperature. The reaction was next concentrated in vacuo and the reaction chromatographed using EtOAc as eluent to yield (S)-2-(4-isopropyl-2-oxo-3-(3-(4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)imidazolidin-1-yl)ethyl 4-methylbenzenesulfonate (0.14 g, 68.7%).

Workup

  1. concentrationThe reaction was next concentrated in vacuo
  2. customthe reaction chromatographed

Sources & evidence

ORD record
ord-7c189dcd682c4ef29162dae9a645754b
Source dataset
uspto-grants-2014_10
Patent number
US08865726B2

Reaction notes

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