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

HRID 1666064
Notes
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Reaction equation

HRID 1666064 reaction equation
Cl[C:2]1[N:9]=[C:8]([N:10]([CH2:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH3:11])[C:7]([F:17])=[CH:6][C:3]=1[C:4]#[N:5].[NH2:18][C:19]1[CH:20]=[C:21]([CH:27]=[CH:28][C:29]=1[CH3:30])[C:22]([NH:24][O:25][CH3:26])=[O:23].[F-].[K+]>CS(C)=O>[C:4]([C:3]1[C:2]([NH:18][C:19]2[CH:20]=[C:21]([CH:27]=[CH:28][C:29]=2[CH3:30])[C:22]([NH:24][O:25][CH3:26])=[O:23])=[N:9][C:8]([N:10]([CH2:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH3:11])=[C:7]([F:17])[CH:6]=1)#[N:5]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 522689Potassium FluorideHCID 207670003-Amino-N-methoxy-4-methylbenzamideHCID 865887972-Chloro-6-[(2,2-dimethyl-propyl)-methyl-amino]-5-fluoro-nicotinonitrile

Product 1

HCID 589285553-{3-Cyano-6-[(2,2-dimethyl-propyl)-methyl-amino]-5-fluoro-pyridin-2-ylamino}-N-methoxy-4-methyl-benzamideYield 4%

Reagents, catalysts & solvents 1

HCID 679
Dimethyl Sulfoxide
Solvent

Conditions

Temperature
150 °C

Procedure

A mixture of 2-chloro-6-[(2,2-dimethyl-propyl)-methyl-amino]-5-fluoro-nicotinonitrile (120 mg, 0.47 mmol), 3-amino-N-methoxy-4-methyl-benzamide (120 mg, 0.66 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 down 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 (7.5 mg, 4%) was obtained after purification by silica gel chromatography with 30% EtOAc in hexane as eluent. C21H26FN5O2 MS m/e=400 (M+H).

Workup

  1. temperatureto cool down 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-77519ccfb71949f79ee1566220b2e170
Source dataset
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08044040B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes