Cyclopropylamine → HCID 62494157, compound

HRID 1910687Notes

Reaction equation

HRID 1910687 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:7](F)=[CH:8][CH:9]=1)[C:5]#[N:6].CC[N:13]([CH:17]([CH3:19])[CH3:18])C(C)C.C1(N)CC1>CN1CCCC1=O>[Cl:1][C:2]1[CH:9]=[CH:8][C:7]([NH:13][CH:17]2[CH2:19][CH2:18]2)=[C:4]([CH:3]=1)[C:5]#[N:6]

Participants

5

Reactant 3

HCID 69828CyclopropylamineHCID 81531DiisopropylethylamineHCID 936535-Chloro-2-fluorobenzonitrile

Product 1

HCID 62494157HCID 62494157, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of 3-chloro-6-fluorobenzonitrile (5 g), Hunig's base (5.60 mL, 1 eq), and cyclopropylamine (3.34 mL, 1.5 eq) in anhydrous N-methylpyrrolidinone (16 mL) was heated to 110° C. for 18 h in a sealed tube. The mixture was then cooled to room temperature and partitioned between ethyl acetate and aqueous sodium bicarbonate. The organic layer was washed once with water, then brine, then concentrated and the residue was washed with hexanes delivering the product as a crystalline white solid (4.66 g, 75% yield). 1H-NMR (300 MHz, DMSO-d6) δ 7.58 (s, 1H), 7.46 (dd, 1H), 7.02 (d, 1H), 6.70 (s, 1H), 2.40 (m, 1H), 0.75 (m, 2H), 0.50 (m, 2H).

Workup

  1. custompartitioned between ethyl acetate and aqueous sodium bicarbonate
  2. washThe organic layer was washed once with water
  3. concentrationbrine, then concentrated

Sources & evidence

ORD record
ord-b7a486a0695b4d9ca2a47658ff26c0a7
Source dataset
uspto-grants-2013_12
Patent number
US08604023B2

Reaction notes

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