Isopropylamine → HCID 11552079, compound

HRID 550358Notes

Reaction equation

HRID 550358 reaction equation
[Cl:1][C:2]1[C:11]([C:12]2[C:17]([F:18])=[CH:16][C:15]([F:19])=[CH:14][C:13]=2[F:20])=[C:10](Cl)[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[CH:22]([NH2:25])([CH3:24])[CH3:23].C(N(C(C)C)C(C)C)C>CN(C=O)C>[Cl:1][C:2]1[C:11]([C:12]2[C:17]([F:18])=[CH:16][C:15]([F:19])=[CH:14][C:13]=2[F:20])=[C:10]([NH:25][CH:22]([CH3:24])[CH3:23])[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

5

Reactant 3

HCID 6363IsopropylamineHCID 81531DiisopropylethylamineHCID 58617239HCID 58617239, compound

Product 1

HCID 11552079HCID 11552079, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The product from Step 3 (0.12 g), isopropylamine (0.3 ml) and N-ethyl-diisopropylamine (0.10 g) were refluxed in DMF (8 ml) in a sealed tube at 50° C. for 17 hours. The dark coloured reaction mixture was evaporated to give an oil, which was purified by flash column chromatography on silica gel (40-60, ethyl acetate/hexane 1/3) to give [2-chloro-3-(2,4,6-trifluorophenyl)-[1,8]naphthyridin-4-yl]-isopropylamine as white crystals (0.059 g, 46%), m.p. 193° C.

Workup

  1. customreaction mixture
  2. customwas evaporated
  3. customto give an oil, which
  4. customwas purified by flash column chromatography on silica gel (40-60, ethyl acetate/hexane 1/3)

Sources & evidence

ORD record
ord-c7371158763f49ca975ec6bc5ef29ba4
Source dataset
uspto-grants-2011_05
Patent number
US07947679B2

Reaction notes

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