4-Fluorobenzoyl chloride → HCID 140686682, compound

HRID 1051405Notes

Reaction equation

HRID 1051405 reaction equation
[F:1][C:2]([F:27])([F:26])[CH:3]([CH2:9][N:10]1[CH2:15][CH2:14][CH2:13][CH:12]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=2)[CH2:11]1)[CH2:4]/[C:5](=[N:7]/[OH:8])/[NH2:6].CCN(C(C)C)C(C)C.[F:37][C:38]1[CH:46]=[CH:45][C:41]([C:42](Cl)=[O:43])=[CH:40][CH:39]=1>C(Cl)Cl>[F:37][C:38]1[CH:46]=[CH:45][C:41]([C:42]([NH:6]/[C:5](=[N:7]\[OH:8])/[CH2:4][CH:3]([CH2:9][N:10]2[CH2:15][CH2:14][CH2:13][CH:12]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:23])([F:24])[F:25])[CH:17]=3)[CH2:11]2)[C:2]([F:1])([F:26])[F:27])=[O:43])=[CH:40][CH:39]=1

Participants

5

Reactant 3

HCID 678794-Fluorobenzoyl chlorideHCID 81531DiisopropylethylamineHCID 90133754HCID 90133754, compound

Product 1

HCID 140686682HCID 140686682, compoundYield 76.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In a 10 mL round-bottomed flask, (Z)-4,4,4-trifluoro-N′-hydroxy-3-((3-(3-(trifluoromethyl)phenyl)-piperidin-1-yl)methyl)butanimidamide (120 mg, 302 μmol) and DIEA (117 mg, 158 μl, 906 μmol) were combined with CH2Cl2 (2.00 ml) to give a colorless solution. 4-Fluorobenzoyl chloride (47.9 mg, 302 μmol) in CH2Cl2 (1 ml) was added drop-wise and the resulting mixture was stirred at room temperature overnight. The crude reaction mixture was concentrated in vacuo to afford 120 mg (38%) of (Z)-4-fluoro-N-(4,4,4-trifluoro-1-(hydroxyimino)-3-((3-(3-(trifluoromethyl)phenyl)piperidin-1-yl)methyl)butyl)benzamide and used as is. MH+=520.

Workup

  1. customto give a colorless solution
  2. customThe crude reaction mixture
  3. concentrationwas concentrated in vacuo

Sources & evidence

ORD record
ord-287bc71dfb31474c9903600baead8c19
Source dataset
uspto-grants-2016_07
Patent number
US09388172B2

Reaction notes

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