Isopropylamine → HCID 67213127, compound

HRID 2223825Notes

Reaction equation

HRID 2223825 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)[N:5]=[C:4]([NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:3]=1.[CH:23]([N:26](C(C)C)CC)([CH3:25])[CH3:24].C(N)(C)C.C(OC(=O)C)C.Cl>C(#N)C.C(OCC)(=O)C.O>[ClH:1].[F:15][C:12]1[CH:13]=[CH:14][C:9]([NH:8][C:6]2[N:7]=[C:2]([NH:26][CH:23]([CH3:25])[CH3:24])[N:3]=[C:4]([NH:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[N:5]=2)=[CH:10][CH:11]=1

Participants

8

Reactant 4

HCID 6363IsopropylamineHCID 81531DiisopropylethylamineHCID 21866389Hydrogen chloride-ethyl acetateHCID 230331686-Chloro-N~2~-(4-fluorophenyl)-N~4~-phenyl-1,3,5-triazine-2,4-diamine

Product 1

HCID 67213127HCID 67213127, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A 316 mg portion of the 6-chloro-N-(4-fluorophenyl)-N′-phenyl-1,3,5-triazine-2,4-diamine was dissolved in 10.0 ml of acetonitrile, and 0.523 ml of diisopropylethylamine and 0.170 ml of isopropylamine were added thereto and stirred overnight at 80° C. The reaction solution was cooled down to room temperature, and then mixed with water and extracted with ethyl acetate. The organic layer was washed with 5% citric acid aqueous solution and saturated brine and then dried using anhydrous magnesium sulfate. The solvent was evaporated under a reduced pressure, and the thus obtained residue was applied to a silica gel column chromatography and eluted with ethyl acetate:n-hexane (2:1) to obtain a crude product. This crude product was dissolved in ethyl acetate and mixed with 4 M hydrochloric acid ethyl acetate solution, the solvent was evaporated under a reduced pressure, and the thus obtained residue was crystallized from ethyl acetate, thereby obtaining 327 mg of N-(4-fluorophenyl)-N′-isopropyl-N″-phenyl-1,3,5-triazine-2,4,6-triamine hydrochloride as colorless crystals.

Workup

  1. temperatureThe reaction solution was cooled down to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with 5% citric acid aqueous solution and saturated brine
  4. customdried
  5. customThe solvent was evaporated under a reduced pressure
  6. washeluted with ethyl acetate:n-hexane (2:1)
  7. customto obtain a crude product
  8. customthe solvent was evaporated under a reduced pressure
  9. customthe thus obtained residue was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-b00f82baa3414430b2026aca16c39aaa
Source dataset
uspto-grants-2008_05
Patent number
US07375222B2

Reaction notes

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