2-Chloroethylamine hydrochloride → HCID 21949846, compound

HRID 558293Notes

Reaction equation

HRID 558293 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-e415e67eb3c64d8284e9bcaf67516708
Source dataset
uspto-grants-2011_11
Patent number
US08063044B2

Reaction notes

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