Nicotinic Acid → HCID 19008885, compound

HRID 1742213Notes

Reaction equation

HRID 1742213 reaction equation
[C:1]([OH:9])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.CN(C=O)C.[CH2:15]([NH:17][CH2:18][CH:19]1[CH2:24][CH2:23][N:22]([C:25]2[CH:30]=[CH:29][N:28]=[C:27]([C:31]([F:34])([F:33])[F:32])[N:26]=2)[CH2:21][CH2:20]1)[CH3:16].C(=O)([O-])[O-].[Na+].[Na+].S(Cl)([Cl:43])=O>>[ClH:43].[CH2:15]([N:17]([CH2:18][CH:19]1[CH2:20][CH2:21][N:22]([C:25]2[CH:30]=[CH:29][N:28]=[C:27]([C:31]([F:34])([F:33])[F:32])[N:26]=2)[CH2:23][CH2:24]1)[C:1]([C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1)=[O:9])[CH3:16]

Participants

6

Reactant 5

HCID 938Nicotinic AcidHCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 24386Thionyl ChlorideHCID 19008881HCID 19008881, compound

Product 1

HCID 19008885HCID 19008885, compoundYield 67%

Procedure

Nicotinic acid (6.16 g, 50 mmole) was refluxed in thionyl chloride (40 ml) for 3 hr. The excess thionyl chloride was removed in vacuo to give a white powder. DMF (90 ml) was added, followed by N-Ethyl-N-[[1-[2-(trifluoromethyl)-4-pyrimidinyl]-4-piperidinyl]methyl]amine (9.75 g, 33.8 mmole) and sodium carbonate (10.6 g, 100 mmole). The mixture was stirred for 18 hr and then was filtered and concentrated in vacuo. The residue was chromatographed on silica gel using 5% methanol/ethyl acetate to give formula I product (8.9 g, 67%). The free base was converted to the hydrochloride salt using excess ethanolic HCl to give a light brown powder (mp: 79°-110°).

Workup

  1. customThe excess thionyl chloride was removed in vacuo
  2. customto give a white powder
  3. filtrationwas filtered
  4. concentrationconcentrated in vacuo
  5. customThe residue was chromatographed on silica gel using 5% methanol/ethyl acetate

Sources & evidence

ORD record
ord-463d631de81f4180b774f365ba773fb9
Source dataset
uspto-grants-1994_08
Patent number
US05338738

Reaction notes

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