2-Chloroethylamine hydrochloride → HCID 21949846, compound

HRID 2215335Notes

Reaction equation

HRID 2215335 reaction equation
Cl.Cl[CH2:3][CH2:4][NH2:5].[CH:6]1([C:9]2[C:13]([O:14][C:15]3[CH:16]=[C:17]([C:23]#[N:24])[CH:18]=[C:19]([CH:22]=3)[C:20]#[N:21])=[C:12]([CH:25]3[CH2:27][CH2:26]3)[NH:11][N:10]=2)[CH2:8][CH2:7]1>>[NH3:5].[NH2:5][CH2:4][CH2:3][N:10]1[C:9]([CH:6]2[CH2:8][CH2:7]2)=[C:13]([O:14][C:15]2[CH:22]=[C:19]([C:20]#[N:21])[CH:18]=[C:17]([CH:16]=2)[C:23]#[N:24])[C:12]([CH:25]2[CH2:27][CH2:26]2)=[N:11]1

Participants

4

Reactant 2

HCID 97937372-Chloroethylamine hydrochlorideHCID 21949817HCID 21949817, compound

Product 2

HCID 222AmmoniaHCID 21949846HCID 21949846, compoundYield 3.3%

Procedure

2-Chloroethylamine hydrochloride (192 mg, 1.65 mmol) and the pyrazole from Example 189 (440 mg, 1.50 mmol) were heated as a melt at 160° C. for 18 hours and the residue was partitioned between dichloromethane (25 ml) and 10% aqueous potassium carbonate solution (25 ml). The organic phase was dried over magnesium sulphate, concentrated under reduced pressure and the residue was purified by flash chromatography on silica gel eluting with dichloromethane:methanol:0.88 ammonia (95:5:0 changing to 95:5:0.5, by volume) to provide the title compound (9.2 mg) as a white solid, m.p. 175–177° C.

Workup

  1. customthe residue was partitioned between dichloromethane (25 ml) and 10% aqueous potassium carbonate solution (25 ml)
  2. dry with materialThe organic phase was dried over magnesium sulphate
  3. concentrationconcentrated under reduced pressure
  4. customthe residue was purified by flash chromatography on silica gel eluting with dichloromethane

Sources & evidence

ORD record
ord-b68ddb2c2744498fb062e8e0371ec8f7
Source dataset
uspto-grants-2006_09
Patent number
US07109228B2

Reaction notes

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