Hydrochloric Acid → HCID 178480709, compound

HRID 639367Notes

Reaction equation

HRID 639367 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[C:9]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=3)=[N:10][NH:11][CH:12]=2)[CH:5]=[CH:4][N:3]=1.[CH3:20][N:21]1[CH2:26][CH2:25][N:24]([C:27]2[CH:32]=[CH:31][C:30]([NH2:33])=[CH:29][CH:28]=2)[CH2:23][CH2:22]1.Cl>>[Cl:19][C:16]1[CH:17]=[CH:18][C:13]([C:9]2[C:8]([C:6]3[CH:5]=[CH:4][N:3]=[C:2]([NH:33][C:30]4[CH:29]=[CH:28][C:27]([N:24]5[CH2:23][CH2:22][N:21]([CH3:20])[CH2:26][CH2:25]5)=[CH:32][CH:31]=4)[N:7]=3)=[CH:12][NH:11][N:10]=2)=[CH:14][CH:15]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 7372534-(4-Methylpiperazin-1-yl)anilineHCID 178477996HCID 178477996, compound

Product 1

HCID 178480709HCID 178480709, compound

Conditions

Temperature
100 °C

Procedure

The solution of 150 mg (0.515 mMol) of 2-chloro-4-[3-(4-chloro-phenyl)-1H-pyrazol-4-yl]-pyrimidine in 5 mL of 1,4-dioxanes (Merck p.a. 9671) at rt is treated with 99 mg of 4-(4-methyl-piperazin-1-yl)-phenylamine (0,515 mMol, 1 Eq.) and 235 mg (2.06 mMol; 202 μl; 4 Eq.) of HCl (32%) (Fluka puriss 84416). The yellow suspension is stirred for 24 h at 100° C. After cooling to rt, the supernatant is decanted and discarded. The smeary residue is treated with 10 ml of NaHCO3 satd. solution and 10 ml of ethyl acetates. The precipitated crude product is filtered off and dried at 60° C. under reduced pressure. The combined organic layers are re-extracted with water, dried (Na2SO4), and evaporated to obtain additional crude product. The combined crude products are purified by means of column chromatography over silica gel (Si60 (0,040-0,063 mm) Merck); eluting with CH2Cl2/CH3OH/NH4OH (9:1:0.1). Final purification is done by suspending the obtained beige crystals in CH2Cl2/CH3OH (1:1) to obtain {4-[3-(4-chloro-phenyl)-1H-pyrazol-4-yl]-pyrimidin-2-yl}-[4-(4-methyl-piperazin-1-yl)-phenyl]-amine as pure crystals.

Workup

  1. temperatureAfter cooling to rt
  2. customthe supernatant is decanted
  3. additionThe smeary residue is treated with 10 ml of NaHCO3
  4. customThe precipitated crude product
  5. filtrationis filtered off
  6. customdried at 60° C. under reduced pressure
  7. extractionThe combined organic layers are re-extracted with water
  8. dry with materialdried (Na2SO4)
  9. customevaporated
  10. customto obtain additional crude product
  11. customare purified by means of column chromatography over silica gel (Si60 (0,040-0,063 mm) Merck)
  12. washeluting with CH2Cl2/CH3OH/NH4OH (9:1:0.1)
  13. customFinal purification

Sources & evidence

ORD record
ord-d7ccb3a3dea6425fb810b12b10b6eab1
Source dataset
uspto-grants-2010_04
Patent number
US07691855B2

Reaction notes

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