Diisopropylamine → (S)-tert-butyl (1-(pyrazolo[1,5-a]pyrazin-4-yl)pyrrolidin-3-yl)carbamate

HRID 1755237Notes

Reaction equation

HRID 1755237 reaction equation
[NH:1]1[CH2:5][CH2:4][C@H:3]([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10])[CH2:2]1.C(NC(C)C)(C)C.Cl[C:22]1[C:23]2[N:24]([N:28]=[CH:29][CH:30]=2)[CH:25]=[CH:26][N:27]=1>CN1C(=O)CCC1>[N:28]1[N:24]2[CH:25]=[CH:26][N:27]=[C:22]([N:1]3[CH2:5][CH2:4][C@H:3]([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:10])([CH3:12])[CH3:11])[CH2:2]3)[C:23]2=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 7912DiisopropylamineHCID 1514396(3S)-(-)-3-(tert-Butoxycarbonylamino)pyrrolidineHCID 722131774-Chloropyrazolo[1,5-a]pyrazine

Product 1

HCID 75204198(S)-tert-butyl (1-(pyrazolo[1,5-a]pyrazin-4-yl)pyrrolidin-3-yl)carbamateYield 91%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a solution of (S)-tert-butyl pyrrolidin-3-ylcarbamate (0.50 g, 2.7 mmol, 1 eq) and diisopropylamine (0.66 mL, 3.8 mmol, 1.4 eq) in 0.2 mL of NMP was added 4-chloropyrazolo[1,5-a]pyrazine (0.47 mL, 3.1 mmol, 1.1 eq). After stirring for 1 h at room temperature, the mixture was concentrated and purified by silica gel column chromatography (100% EtOAc) to afford (S)-tert-butyl (1-(pyrazolo[1,5-a]pyrazin-4-yl)pyrrolidin-3-yl)carbamate (0.740 g, 2.4 mmol, 91%).

Workup

  1. concentrationthe mixture was concentrated
  2. custompurified by silica gel column chromatography (100% EtOAc)

Sources & evidence

ORD record
ord-21415056793243d2a7b46fba7841ea10
Source dataset
uspto-grants-2015_10
Patent number
US09169261B2

Reaction notes

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