HCID 19862162, compound → HCID 66745521, compound

HRID 1961481Notes

Reaction equation

HRID 1961481 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8][C:9](=O)[C:10](C)(C)C)C=1C=O.O=[C:18]([CH3:34])[CH2:19][C:20]([NH:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[CH:25]=1)=[O:21].C[Si](C)(C)N[Si](C)(C)C.[K]>C1COCC1.[NH4+].[Cl-]>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[C:34]=1[CH:18]=[C:19]([C:20]([NH:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[CH:25]=1)=[O:21])[C:9]([CH3:10])=[N:8]2

Participants

6

Reactant 3

HCID 19862162HCID 19862162, compoundHCID 44602630N-(4-Chloro-3-formylpyridin-2-yl)-2,2-dimethylpropanamideHCID 45051783Silanamine, 1,1,1-trimethyl-N-(trimethylsilyl)-, potassium salt

Product 1

HCID 66745521HCID 66745521, compoundYield 80.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
0 °C

Procedure

N-(4-Chloro-3-formylpyridin-2-yl)pivalamide (678 mg, 2.82 mmol) and 3-oxo-N-(3-(trifluoromethyl)benzyl)butanamide (2.82 mmol) was dissolved in dry THF (25 ml) and cooled to 0° C. under an atmosphere of nitrogen. Potassium hexamethyldisilazane (14 ml, 7.0 mmol, 0.5 M in toluene) was added dropwise under 15 minutes and the reaction was stirred at 0° C. for 15 minutes followed by 18 hours at room temperature. Reaction was then diluted with NH4Cl (50 ml, sat aq) and extracted with CH2Cl2 (3*30 ml). Combined organics were dried over MgSO4, filtered and evaporated. The crude product was purified by flash chromatography using CH2Cl2/CH3OH (20:1) as eluent to give 0.86 g (80%) of 5-chloro-2-methyl-N-(3-(trifluoromethyl)benzyl)-1,8-naphthyridine-3-carboxamide as a pale syrup.

Workup

  1. waitfollowed by 18 hours at room temperature
  2. customReaction
  3. extractionextracted with CH2Cl2 (3*30 ml)
  4. dry with materialCombined organics were dried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-cb6c7bf04c1440889eed1c149ed58b3e
Source dataset
uspto-grants-2013_04
Patent number
US08415333B2

Reaction notes

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