Methylamine → HCID 86711547, compound

HRID 512509Notes

Reaction equation

HRID 512509 reaction equation
[F:1][CH:2]([F:20])[C:3]1[CH:4]=[C:5]([C:9]2[C:10](=[O:19])[C:11]([C:16](O)=[O:17])=[CH:12][NH:13][C:14]=2[CH3:15])[CH:6]=[CH:7][CH:8]=1.[CH3:21][N:22](C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(CC)CC)C.CN>CN(C=O)C>[CH3:21][NH:22][C:16]([C:11]1[C:10](=[O:19])[C:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([CH:2]([F:20])[F:1])[CH:4]=2)=[C:14]([CH3:15])[NH:13][CH:12]=1)=[O:17]

Participants

6

Reactant 4

HCID 6329MethylamineHCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 86711548HCID 86711548, compound

Product 1

HCID 86711547HCID 86711547, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 5-(3-difluoromethyl-phenyl)-6-methyl-4-oxo-1,4-dihydro-pyridine-3-carboxylic acid (preparation 16a, 931 mg, 3.33 mmol), TBTU (1.17 g, 3.64 mmol), triethylamine (0.94 mL, 6.70 mmol) in DMF (3 mL) is stirred for 30 min. Then, methylamine (5.23 mL of 2M solution in THF, 10.5 mmol) is added and the reaction mixture is stirred for 18 h at room temperature. The reaction mixture is concentrated under reduced pressure and purified by preparative reversed-phase HPLC (XBridge, gradient of acetonitrile in water, 0.3% NH4OH, 60° C.). Yield: 0.25 g (25% of theory); ESI mass spectrum: [M+H]+=293; Retention time HPLC: 0.59 min (Z011_S03).

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure
  2. custompurified by preparative reversed-phase HPLC (XBridge, gradient of acetonitrile in water, 0.3% NH4OH, 60° C.)
  3. custom0.59 min (Z011_S03)

Sources & evidence

ORD record
ord-7a34f2ca3ecf41d9a312418329caa10d
Source dataset
uspto-grants-2015_08
Patent number
US09102624B2

Reaction notes

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