Acetyl chloride → 2-(6-chloro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (1-azetidin-3-yl-ethyl)-amide hydrochloride

HRID 245983Notes

Reaction equation

HRID 245983 reaction equation
C(OC([N:8]1[CH2:11][CH:10]([CH:12]([NH:14][C:15]([C:17]2[C:25]3[C:20](=[N:21][CH:22]=[C:23]([C:26]4[C:34]5[C:29](=[CH:30][C:31]([Cl:35])=[CH:32][CH:33]=5)[N:28]([CH3:36])[N:27]=4)[N:24]=3)[N:19]([CH2:37][O:38][CH2:39][CH2:40][Si:41]([CH3:44])([CH3:43])[CH3:42])[CH:18]=2)=[O:16])[CH3:13])[CH2:9]1)=O)(C)(C)C.C(Cl)(=O)C>CO>[ClH:35].[NH:8]1[CH2:9][CH:10]([CH:12]([NH:14][C:15]([C:17]2[C:25]3[C:20](=[N:21][CH:22]=[C:23]([C:26]4[C:34]5[C:29](=[CH:30][C:31]([Cl:35])=[CH:32][CH:33]=5)[N:28]([CH3:36])[N:27]=4)[N:24]=3)[N:19]([CH2:37][O:38][CH2:39][CH2:40][Si:41]([CH3:42])([CH3:44])[CH3:43])[CH:18]=2)=[O:16])[CH3:13])[CH2:11]1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 712802663-(1-{[2-(6-chloro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carbonyl]-amino}-ethyl)-azetidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 866779292-(6-chloro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (1-azetidin-3-yl-ethyl)-amide hydrochlorideYield 218.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-(1-{[2-(6-chloro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanylethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carbonyl]-amino}-ethyl)-azetidine-1-carboxylic acid tert-butyl ester (150 mg, 0.23 mmol) in MeOH (4 mL) at 0° C. was added acetyl chloride (0.33 mL, 4.69 mmol) dropwise over 5 min. The reaction mixture was stirred at room temperature for 1 h as a thick precipitate gradually formed. The solvent was evaporated at room temperature and the residue was dried under high vacuum to isolate 145 mg of 2-(6-chloro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (1-azetidin-3-yl-ethyl)-amide hydrochloride as a yellow solid.

Workup

  1. customgradually formed
  2. customThe solvent was evaporated at room temperature
  3. customthe residue was dried under high vacuum

Sources & evidence

ORD record
ord-c5dbf0a017334cb398007611a7c98a55
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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