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Acetyl chloride → N-[6-aminopyrid-3-yl]-5-fluoro-1-[(3-fluorophenyl)methyl]-1H-indole-2-carboxamide

HRID 1943989
Notes
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Reaction equation

HRID 1943989 reaction equation
C([NH:4][C:5]1[N:10]=[CH:9][C:8]([NH:11][C:12]([C:14]2[N:15]([CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[CH:26]=3)[C:16]3[C:21]([CH:22]=2)=[CH:20][C:19]([F:23])=[CH:18][CH:17]=3)=[O:13])=[CH:7][CH:6]=1)(=O)C.C(Cl)(=O)C>CO.C([O-])(O)=O.[Na+].C(OCC)(=O)C>[NH2:4][C:5]1[N:10]=[CH:9][C:8]([NH:11][C:12]([C:14]2[N:15]([CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[CH:26]=3)[C:16]3[C:21]([CH:22]=2)=[CH:20][C:19]([F:23])=[CH:18][CH:17]=3)=[O:13])=[CH:7][CH:6]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 6367Acetyl chlorideHCID 66863369N-[6-(Acetylamino)pyridin-3-yl]-5-fluoro-1-(3-fluorobenzyl)-1H-indole-2-carboxamide

Product 1

HCID 66863527N-[6-aminopyrid-3-yl]-5-fluoro-1-[(3-fluorophenyl)methyl]-1H-indole-2-carboxamideYield 85%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8857
Ethyl Acetate
Solvent
HCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of 0.6 g (1.43 mmol) of N-[6-(acetylamino)pyrid-3-yl]-5-fluoro-1-[(3-fluorophenyl)methyl]-1H-indole-2-carboxamide, prepared according to the protocol described in step 4.1, in 9 mL of anhydrous methanol, stirred at 0° C. under an inert atmosphere, are added dropwise 2.03 mL (28.54 mmol) of acetyl chloride. The reaction mixture is stirred at 0° C. for 30 minutes and then gradually brought to 70° C. and stirred for 48 hours. The reaction mixture is concentrated to dryness. The residue obtained is taken up in a mixture of 200 mL of saturated aqueous NaHCO3 solution and 200 mL of ethyl acetate. The phases are separated by settling and the aqueous phase is extracted with 200 mL of ethyl acetate. The combined organic phases are dried over sodium sulfate and then concentrated under reduced pressure. 0.46 g of the expected product is thus obtained.

Workup

  1. customprepared
  2. stirringThe reaction mixture is stirred at 0° C. for 30 minutes
  3. customgradually brought to 70° C.
  4. stirringstirred for 48 hours
  5. concentrationThe reaction mixture is concentrated to dryness
  6. customThe residue obtained
  7. customThe phases are separated
  8. extractionthe aqueous phase is extracted with 200 mL of ethyl acetate
  9. dry with materialThe combined organic phases are dried over sodium sulfate
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e1a1f2a2b95d4651ad20d0fa440de22d
Source dataset
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08394820B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes