Diisopropylethylamine → HCID 86693784, compound

HRID 245075

Reaction equation

HRID 245075 reaction equation
[Cl:1][C:2]1[C:9]([CH3:10])=[C:8](F)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].C(N(C(C)C)CC)(C)C.Cl.[NH2:22][C@@H:23]1[CH2:28][CH2:27][CH2:26][CH2:25][C@@H:24]1[OH:29]>ClCCl>[Cl:1][C:2]1[C:9]([CH3:10])=[C:8]([NH:22][C@@H:23]2[CH2:28][CH2:27][CH2:26][CH2:25][C@@H:24]2[OH:29])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 17039400(1S,2R)-2-aminocyclohexan-1-ol hydrochlorideHCID 445509712-Chloro-4-fluoro-3-methylbenzonitrile

Product 1

HCID 86693784HCID 86693784, compoundYield 29.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-chloro-4-fluoro-3-methyl-benzonitrile (500 mg, 2.95 mmol), diisopropylethylamine (1.29 mL, 7.37 mmol), and (1S,2R)-2-aminocyclohexanol hydrochloride (670 mg, 4.42 mmol, Acros®) is microwaved using a CEM® microwave at 190° C. for 2 h and 180° C. for 4 h. The mixture is diluted with dichloromethane and washed with 1 N HCl. The aqueous layer is extracted again with dichloromethane. The combined organic phases are dried over sodium sulfate, filtered, and concentrated in vacuo. The resulting residue is purified using radial chromatography, eluting with 2% methanol/dichloromethane. The isolated product is recrystallized with ether and hexane to yield the title compound as a white solid (231 mg, 29%). LC-ES/MS m/z 265.0 (M+1).

Workup

  1. customis microwaved
  2. customat 190° C.
  3. customfor 2 h
  4. washwashed with 1 N HCl
  5. extractionThe aqueous layer is extracted again with dichloromethane
  6. dry with materialThe combined organic phases are dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe resulting residue is purified
  10. washeluting with 2% methanol/dichloromethane
  11. customThe isolated product is recrystallized with ether and hexane

Sources & evidence

ORD record
ord-7392c902ed19404883235588542a6b88
Source dataset
uspto-grants-2014_02
Patent number
US08658693B2

Linked notes

Loading…