Pyrrolidine → (S)-4-isopropyl-1-(2-(pyrrolidin-1-yl)ethyl)-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

HRID 539034Notes

Reaction equation

HRID 539034 reaction equation
C1(S(O[CH2:11][CH2:12][N:13]2[CH2:17][C@H:16]([CH:18]([CH3:20])[CH3:19])[N:15]([C:21]3[CH:26]=[CH:25][N:24]4[N:27]=[CH:28][C:29]([C:30]5[CH:35]=[CH:34][C:33]([C:36]6[N:40]=[CH:39][N:38]([CH2:41][O:42][CH2:43][CH2:44][Si:45]([CH3:48])([CH3:47])[CH3:46])[N:37]=6)=[CH:32][CH:31]=5)=[C:23]4[N:22]=3)[C:14]2=[O:49])(=O)=O)C=CC=CC=1.[NH:50]1[CH2:54][CH2:53][CH2:52][CH2:51]1>>[CH:18]([C@H:16]1[CH2:17][N:13]([CH2:12][CH2:11][N:50]2[CH2:54][CH2:53][CH2:52][CH2:51]2)[C:14](=[O:49])[N:15]1[C:21]1[CH:26]=[CH:25][N:24]2[N:27]=[CH:28][C:29]([C:30]3[CH:31]=[CH:32][C:33]([C:36]4[N:40]=[CH:39][N:38]([CH2:41][O:42][CH2:43][CH2:44][Si:45]([CH3:48])([CH3:47])[CH3:46])[N:37]=4)=[CH:34][CH:35]=3)=[C:23]2[N:22]=1)([CH3:19])[CH3:20]

Participants

3

Reactant 2

HCID 31268PyrrolidineHCID 86667825(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 benzenesulfonate

Product 1

HCID 67033615(S)-4-isopropyl-1-(2-(pyrrolidin-1-yl)ethyl)-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-oneYield 95%

Procedure

To the crude (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 benzenesulfonate from step 1 (5 mL, 0.051 g, 0.071 mmol) was added pyrrolidine (2 mL) and the reaction stirred overnight at ambient temperature. The reaction was concentrated in vacuo and the material taken up in dichloromethane and washed with 1N NaOH. The combined organic layers were concentrated in vacuo and the residue chromatographed using 2% MeOH/dichloromethane to 5% MeOH/dichloromethane to yield (S)-4-isopropyl-1-(2-(pyrrolidin-1-yl)ethyl)-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 (0.041 g, 95%).

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. washwashed with 1N NaOH
  3. concentrationThe combined organic layers were concentrated in vacuo
  4. customthe residue chromatographed

Sources & evidence

ORD record
ord-85becb768a3143adb81daa096e0e606e
Source dataset
uspto-grants-2014_10
Patent number
US08865726B2

Reaction notes

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