2-Chloroethylamine hydrochloride → HCID 9921887, compound

HRID 558268Notes

Reaction equation

HRID 558268 reaction equation
[CH2:1]([C:3]1[C:7]([O:8][C:9]2[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=2)[C:12]#[N:13])=[C:6]([CH2:17][CH3:18])[NH:5][N:4]=1)[CH3:2].[ClH:19].[Cl:20][CH2:21][CH2:22][NH2:23]>C(=O)([O-])O.[Na+]>[Cl:19][CH2:21][Cl:20].[CH3:7][OH:8].[NH3:4].[NH2:23][CH2:22][CH2:21][N:4]1[C:3]([CH2:1][CH3:2])=[C:7]([O:8][C:9]2[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=2)[C:12]#[N:13])[C:6]([CH2:17][CH3:18])=[N:5]1

Participants

5

Reactant 2

HCID 97937372-Chloroethylamine hydrochlorideHCID 9813536HCID 9813536, compound

Product 2

HCID 9921887HCID 9921887, compoundYield 105.2%HCID 21584172Ammonia methanol dichloromethane

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

The pyrazole of Example 60 (200 mg, 0.829 mmol) and 2-chloroethylamine hydrochloride (144 mg, 1.24 mmol) were heated as a melt at 150° C. for 17 hours. After cooling the solid was dissolved in saturated aqueous sodium hydrogencarbonate (15 ml) and extracted with dichloromethane (2×10 ml). The combined organic phases were washed with 2M aqueous hydrochloric acid (20 ml) and the aqueous layer was neutralised with solid sodium carbonate and extracted with dichloromethane (3×10 ml). The combined organic phases were dried over magnesium sulphate, filtered and concentrated under reduced pressure to leave an orange gum. The crude product was purified by flash column chromatography on silica gel eluting with dichloromethane:methanol (90:10) then dichloromethane:methanol:ammonia (90:9:1, by volume) to provide the title compound (124 mg) as a pale yellow oil.

Workup

  1. temperatureAfter cooling the solid
  2. extractionextracted with dichloromethane (2×10 ml)
  3. washThe combined organic phases were washed with 2M aqueous hydrochloric acid (20 ml)
  4. extractionextracted with dichloromethane (3×10 ml)
  5. dry with materialThe combined organic phases were dried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto leave an orange gum
  9. customThe crude product was purified by flash column chromatography on silica gel eluting with dichloromethane:methanol (90:10)

Sources & evidence

ORD record
ord-c00e4571888d44ebab8e44459953ade2
Source dataset
uspto-grants-2011_11
Patent number
US08063044B2

Reaction notes

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