Acetyl chloride → HCID 59540642, compound

HRID 1677505Notes

Reaction equation

HRID 1677505 reaction equation
C(OC(=O)[NH:7][CH2:8][C:9]1([CH3:43])[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]3[N:21]=[C:22]4[C:28]([C:29](=[O:34])[C:30]([CH3:33])([CH3:32])[CH3:31])=[CH:27][N:26](COCC[Si](C)(C)C)[C:23]4=[N:24][CH:25]=3)[CH:15]=2)[CH2:10]1)(C)(C)C.C(Cl)(=O)C>CO>[NH2:7][CH2:8][C:9]1([CH3:43])[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[C:16]([C:20]3[N:21]=[C:22]4[C:28]([C:29](=[O:34])[C:30]([CH3:32])([CH3:31])[CH3:33])=[CH:27][NH:26][C:23]4=[N:24][CH:25]=3)[CH:17]=[CH:18][CH:19]=2)[CH2:10]1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 67346238HCID 67346238, compound

Product 1

HCID 59540642HCID 59540642, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-{2-[3-(3-Aminomethyl-3-methyl-pyrrolidin-1-yl)-phenyl]-5H-pyrrolo[2,3-b]pyrazin-7-yl}-2,2-dimethyl-propan-1-one was prepared following a similar procedure but using (1-{3-[7-(2,2-dimethyl-propionyl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-phenyl}-3-methyl-pyrrolidin-3-ylmethyl)-carbamic acid tert-butyl ester as starting material. In this instance the starting material was taken into a 4/1 mixture of MeOH and acetyl chloride and the reaction mixture was stirred at RT for 2 hours before being evaporated. The residue was taken into 2 mL of concentrated HCl and stirred at RT for 1 hour before being diluted with H2O and neutralized by addition of solid NaOH. The product was obtained in 44% yield after SiO2 chromatography (DCM/[DCM/MeOH/NH4OH 60/10/1] 100-60% DCM).

Workup

  1. custombefore being evaporated
  2. stirringstirred at RT for 1 hour
  3. additionbefore being diluted with H2O
  4. additionneutralized by addition of solid NaOH
  5. customThe product was obtained in 44% yield after SiO2 chromatography (DCM/[DCM/MeOH/NH4OH 60/10/1] 100-60% DCM)

Sources & evidence

ORD record
ord-43c69d64b22043449095bdb16cfe57e9
Source dataset
uspto-grants-2011_08
Patent number
US08008298B2

Reaction notes

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