Acetyl chloride → HCID 67002083, compound

HRID 2191570Notes

Reaction equation

HRID 2191570 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([NH:14][C:15]([C:17]2[C:25]3[C:20](=[N:21][CH:22]=[C:23]([CH:26]4[CH2:28][CH2:27]4)[N:24]=3)[N:19]([CH2:29][O:30][CH2:31][CH2:32][Si:33]([CH3:36])([CH3:35])[CH3:34])[CH:18]=2)=[O:16])[CH2:9]1)=O)(C)(C)C.C([Cl:40])(=O)C>CO>[ClH:40].[NH:8]1[CH2:13][CH2:12][CH2:11][CH:10]([NH:14][C:15]([C:17]2[C:25]3[C:20](=[N:21][CH:22]=[C:23]([CH:26]4[CH2:28][CH2:27]4)[N:24]=3)[N:19]([CH2:29][O:30][CH2:31][CH2:32][Si:33]([CH3:36])([CH3:35])[CH3:34])[CH:18]=2)=[O:16])[CH2:9]1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 58525277HCID 58525277, compound

Product 1

HCID 67002083HCID 67002083, compoundYield 105.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

In a 25 mL round-bottomed flask, 3-{[2-cyclopropyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carbonyl]-amino}-piperidine-1-carboxylic acid tert-butyl ester (0.435 g, 0.84 mmol) was dissolved in MeOH (7 mL). The solution was cooled to 0° C. and acetyl chloride (1.2 mL, 16.8 mmol) was added dropwise over 10 min. The ice bath was removed and the reaction mixture was stirred at room temperature for 1.5 h. The solvent was evaporated at room temperature and the residue was dried under high vacuum to afford 402 mg of 2-cyclopropyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid piperidin-3-ylamide hydrochloride as a light yellow foam which was used without further purification.

Workup

  1. customThe ice bath was removed
  2. customThe solvent was evaporated at room temperature
  3. customthe residue was dried under high vacuum

Sources & evidence

ORD record
ord-374ca83e857d47b39618b80ff0bf638d
Source dataset
uspto-grants-2012_12
Patent number
US08329699B2

Reaction notes

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