2-Chloroethylamine hydrochloride → HCID 21877105, compound

HRID 723610Notes

Reaction equation

HRID 723610 reaction equation
[CH2:1]([C:3]1[C:7]([CH2:8][C:9]2[CH:10]=[C:11]([C:17]#[N:18])[CH:12]=[C:13]([CH:16]=2)[C:14]#[N:15])=[C:6]([CH2:19][CH3:20])[NH:5][N:4]=1)[CH3:2].Cl.Cl[CH2:23][CH2:24][NH2:25]>>[NH3:4].[NH2:25][CH2:24][CH2:23][N:5]1[C:6]([CH2:19][CH3:20])=[C:7]([CH2:8][C:9]2[CH:16]=[C:13]([C:14]#[N:15])[CH:12]=[C:11]([CH:10]=2)[C:17]#[N:18])[C:3]([CH2:1][CH3:2])=[N:4]1

Participants

4

Reactant 2

HCID 97937372-Chloroethylamine hydrochlorideHCID 9943220HCID 9943220, compound

Product 2

HCID 222AmmoniaHCID 21877105HCID 21877105, compoundYield 83%

Conditions

Temperature
150 °C

Procedure

A stirred mixture of the pyrazole (106 mg, 0.4 mmol) of Example 91 and 2-chloroethylamine hydrochloride (70 mg, 0.6 mmol) was heated at 150° C. under nitrogen for 18 hours. After cooling the mixture was partitioned between 10% aqueous potassium carbonate (40 ml) and dichloromethane (40 ml) and the organic layer was dried over magnesium sulphate, filtered and evaporated under reduced pressure. The crude product was purified by flash chromatography on silica gel eluting with a solvent gradient of dichloromethane:methanol (98:2, by volume) and then dichloromethane:methanol:0.880 ammonia (95:5:0.5, by volume) to give the title compound as a white solid (51 mg) m.p. 100–105° C.

Workup

  1. temperatureAfter cooling the mixture
  2. customwas partitioned between 10% aqueous potassium carbonate (40 ml) and dichloromethane (40 ml)
  3. dry with materialthe organic layer was dried over magnesium sulphate
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe crude product was purified by flash chromatography on silica gel eluting with a solvent gradient of dichloromethane:methanol (98:2, by volume)

Sources & evidence

ORD record
ord-33e046d14d684239b8a6787b398d54c9
Source dataset
uspto-grants-2006_11
Patent number
US07141585B2

Reaction notes

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