Acetyl chloride → HCID 75204084, compound

HRID 1755230Notes

Reaction equation

HRID 1755230 reaction equation
C(Cl)(=O)C.[N:5]1[CH:6]=[CH:7][N:8]2[CH:13]=[CH:12][N:11]=[C:10]([N:14]3[CH2:18][CH2:17][C@H:16]([NH:19]C(=O)OC(C)(C)C)[CH2:15]3)[C:9]=12>CO>[N:5]1[CH:6]=[CH:7][N:8]2[CH:13]=[CH:12][N:11]=[C:10]([N:14]3[CH2:18][CH2:17][C@H:16]([NH2:19])[CH2:15]3)[C:9]=12

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 75204083(S)-tert-butyl (1-(imidazo[1,2-a]pyrazin-8-yl)pyrrolidin-3-yl)carbamate

Product 1

HCID 75204084HCID 75204084, compoundYield 432.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of acetyl chloride (114 mL, 1.6 mol) in 290 mL of MeOH at 0° C. was added a solution of (S)-tert-butyl (1-(imidazo[1,2-a]pyrazin-8-yl)pyrrolidin-3-yl)carbamate (111.7 g, 0.37 mol) in 450 mL of MeOH. The reaction mixture was stirred at room temperature for 2 h then heated at 60° C. for 30 min. The product was filtered, washed with 200 mL of MeOH and dried in a vacuum oven to afforded (S)-1-(imidazo[1,2-a]pyrazin-8-yl)pyrrolidin-3-amine (101.2 g, 1.6 mol, 100%).

Workup

  1. temperaturethen heated at 60° C. for 30 min
  2. filtrationThe product was filtered
  3. washwashed with 200 mL of MeOH
  4. customdried in a vacuum oven

Sources & evidence

ORD record
ord-6b9d0d2ee7d74fb69dafff0c8490595c
Source dataset
uspto-grants-2015_10
Patent number
US09169261B2

Reaction notes

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