1,2-Dichloroethane → HCID 86710430, compound

HRID 1398453Notes

Reaction equation

HRID 1398453 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([C:14](O)=[O:15])=[CH:12][N:11]=[CH:10][C:9]=2[F:17])=[C:4]([F:18])[CH:3]=1.C1C=CC2N(O)N=[N:25][C:23]=2C=1.C(Cl)CCl.Cl.CN.CCN(C(C)C)C(C)C>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([C:14]([NH:25][CH3:23])=[O:15])=[CH:12][N:11]=[CH:10][C:9]=2[F:17])=[C:4]([F:18])[CH:3]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 6364545Methylamine hydrochlorideHCID 86695927HCID 86695927, compound

Product 1

HCID 86710430HCID 86710430, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To the solution of 4-(4-chloro-2-fluorophenyl)-5-fluoronicotinic acid (530 mg, 1.966 mmol) in DMF (5 mL) cooled at 0° C., was added HOBT (602 mg, 3.93 mmol) and EDC (565 mg, 2.95 mmol), then the mixture was stirred for 5 min. Methylamine hydrochloride (531 mg, 7.86 mmol) and DIEA (1.030 mL, 5.90 mmol) were added and the resultant mixture was stirred at RT for 12 h. Ice-cold water was added to the reaction and the solid obtained was collected by vacuum filtration. The solid so obtained was washed with water (50 mL) and air dried to afford 4-(4-chloro-2-fluorophenyl)-5-fluoro-N-methylnicotinamide (350 mg, 1.238 mmol, 63% yield) as an orange oil. LC/MS (ESI) m/e 282.9 [(M+H)+, calcd for C13H10ClF2N2O 283.0]; LC/MS retention time (method D): tR=0.83 min.

Workup

  1. additionIce-cold water was added to the reaction
  2. customthe solid obtained
  3. filtrationwas collected by vacuum filtration
  4. customThe solid so obtained
  5. washwas washed with water (50 mL) and air
  6. customdried

Sources & evidence

ORD record
ord-0f9e32c6a3fc4955ba1a16b2686a8bbf
Source dataset
uspto-grants-2014_12
Patent number
US08901305B2

Reaction notes

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