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Potassium Fluoride → 3-{3-Cyano-6-[(2,2-dimethyl-propyl)-amino]-5-fluoro-pyridin-2-ylamino}-N-methoxy-4-methyl-benzamide

HRID 852023
Notes
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Reaction equation

HRID 852023 reaction equation
Cl[C:2]1[N:9]=[C:8]([NH:10][CH2:11][C:12]([CH3:15])([CH3:14])[CH3:13])[C:7]([F:16])=[CH:6][C:3]=1[C:4]#[N:5].[NH2:17][C:18]1[CH:19]=[C:20]([CH:26]=[CH:27][C:28]=1[CH3:29])[C:21]([NH:23][O:24][CH3:25])=[O:22].[F-].[K+]>CS(C)=O>[C:4]([C:3]1[C:2]([NH:17][C:18]2[CH:19]=[C:20]([CH:26]=[CH:27][C:28]=2[CH3:29])[C:21]([NH:23][O:24][CH3:25])=[O:22])=[N:9][C:8]([NH:10][CH2:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[C:7]([F:16])[CH:6]=1)#[N:5]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 522689Potassium FluorideHCID 207670003-Amino-N-methoxy-4-methylbenzamideHCID 865887982-Chloro-6-[(2,2-dimethyl-propyl)-amino]-5-fluoro-nicotinonitrile

Product 1

HCID 101346713-{3-Cyano-6-[(2,2-dimethyl-propyl)-amino]-5-fluoro-pyridin-2-ylamino}-N-methoxy-4-methyl-benzamideYield 1%

Reagents, catalysts & solvents 1

HCID 679
Dimethyl Sulfoxide
Solvent

Conditions

Temperature
150 °C

Procedure

A mixture of 2-chloro-6-[(2,2-dimethyl-propyl)-amino]-5-fluoro-nicotinonitrile (150 mg, 0.62 mmol), 3-amino-N-methoxy-4-methyl-benzamide (150 mg, 0.83 mmol) and potassium fluoride (30 mg, 0.51 mmol) in DMSO (1 mL) was heated to 150° C. overnight. The reaction mixture was allowed to cool to room temp and then partitioned between water and ethyl acetate. The organic layer was dried (sodium sulfate) and concentrated under reduced pressure. The product (2.5 mg, 1%) was obtained after purification by silica gel chromatography with 30% EtOAc in hexane as eluent. C20H24FN5O2 MS m/e=386 (M+H).

Workup

  1. temperatureto cool to room temp
  2. custompartitioned between water and ethyl acetate
  3. dry with materialThe organic layer was dried (sodium sulfate)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d7d86ab8b68c46d4b050f45baeb8f0a4
Source dataset
uspto-grants-2007_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07253174B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes