4-Chlorobutanoic acid → HCID 90020591, compound

HRID 2200149Notes

Reaction equation

HRID 2200149 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:4]=[C:5]([NH2:10])[CH:6]=[C:7]([NH2:9])[CH:8]=1.[Cl:13][CH2:14][CH2:15][CH2:16][C:17](O)=[O:18].ON1C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C>ClCCl>[NH2:9][C:7]1[CH:6]=[C:5]([NH:10][C:17](=[O:18])[CH2:16][CH2:15][CH2:14][Cl:13])[CH:4]=[C:3]([C:2]([F:11])([F:12])[F:1])[CH:8]=1

Participants

6

Reactant 4

HCID 123004-Chlorobutanoic acidHCID 677815-(Trifluoromethyl)benzene-1,3-diamineHCID 757711-HydroxybenzotriazoleHCID 81531Diisopropylethylamine

Product 1

HCID 90020591HCID 90020591, compoundYield 52.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Mix 5-(trifluoromethyl)benzene-1,3-diamine (300 mg, 1.70 mmol), 4-chlorobutanoic acid (230 mg, 1.87 mmol), 1-ethyl-3-(3-dimethyllaminopropyl)carbodiimide hydrochloride (EDCI.HCl, 650 mg, 3.40 mmol), 1-hydroxybenzotriazole (HOBt, 230 mg, 1.70 mmol) and diisopropylethylamine (450 mg, 3.40 mmol) in dichloromethane (10 mL), stir overnight at room temperature. Concentrate the reaction mixture under reduced pressure to obtain the crude product. Purify by flash chromatography (silica gel, PE:EtOAc=1:10) to yield the product (250 mg, 52%). MS: (M+1): 281.2.

Workup

  1. concentrationConcentrate the reaction mixture under reduced pressure
  2. customto obtain the crude product
  3. customPurify by flash chromatography (silica gel, PE:EtOAc=1:10)

Sources & evidence

ORD record
ord-85f6b5985e644cd9bbca875b045ad850
Source dataset
uspto-grants-2016_06
Patent number
US09359338B2

Reaction notes

Loading…