1,1-Dimethylethyl (2R)-2-[[(methylsulfonyl)oxy]methyl]-1-pyrrolidinecarboxylate → (R)-tert-butyl 2-(((S)-3-(3-bromopyrazolo[1,5-a]pyrimidin-5-yl)-4-isopropyl-2-oxoimidazolidin-1-yl)methyl)pyrrolidine-1-carboxylate

HRID 539063Notes

Reaction equation

HRID 539063 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][N:5]2[CH:10]=[CH:9][C:8]([N:11]3[C@@H:15]([CH:16]([CH3:18])[CH3:17])[CH2:14][NH:13][C:12]3=[O:19])=[N:7][C:6]=12.CS(O[CH2:25][C@H:26]1[CH2:30][CH2:29][CH2:28][N:27]1[C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])(=O)=O>>[Br:1][C:2]1[CH:3]=[N:4][N:5]2[CH:10]=[CH:9][C:8]([N:11]3[C@@H:15]([CH:16]([CH3:17])[CH3:18])[CH2:14][N:13]([CH2:25][C@H:26]4[CH2:30][CH2:29][CH2:28][N:27]4[C:31]([O:33][C:34]([CH3:35])([CH3:37])[CH3:36])=[O:32])[C:12]3=[O:19])=[N:7][C:6]=12

Participants

3

Reactant 2

HCID 130087591,1-Dimethylethyl (2R)-2-[[(methylsulfonyl)oxy]methyl]-1-pyrrolidinecarboxylateHCID 67033394HCID 67033394, compound

Product 1

HCID 67034293(R)-tert-butyl 2-(((S)-3-(3-bromopyrazolo[1,5-a]pyrimidin-5-yl)-4-isopropyl-2-oxoimidazolidin-1-yl)methyl)pyrrolidine-1-carboxylateYield 50%

Procedure

(R)-tert-butyl 2-(((S)-3-(3-bromopyrazolo[1,5-a]pyrimidin-5-yl)-4-isopropyl-2-oxoimidazolidin-1-yl)methyl)pyrrolidine-1-carboxylate (94 mg, 50%) was prepared by the procedure described in Example 38, Step 1, using (S)-1-(3-bromopyrazolo[1,5-a]pyrimidin-5-yl)-5-isopropylimidazolidin-2-one and (R)-tert-butyl 2-((methylsulfonyloxy)methyl)pyrrolidine-1-carboxylate.

Sources & evidence

ORD record
ord-8eed8ba4e67d422a9645b50cd368f871
Source dataset
uspto-grants-2014_10
Patent number
US08865726B2

Reaction notes

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