Water → HCID 10927071, compound

HRID 2306854Notes

Reaction equation

HRID 2306854 reaction equation
[Cl:1][C:2]1[C:3]([CH2:12][NH2:13])=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[F:14][C:15]([F:26])([F:25])[C:16]1[CH:24]=[CH:23][CH:22]=[CH:21][C:17]=1[C:18](Cl)=[O:19].C(N(CC)CC)C.O>CCOCC.C(OCC)(=O)C>[Cl:1][C:2]1[C:3]([CH2:12][NH:13][C:18]([C:17]2[C:16]([C:15]([F:14])([F:25])[F:26])=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:19])=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:9])[F:10])[CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 675612-(Trifluoromethyl)benzoyl chlorideHCID 11085087(3-Chloro-5-(trifluoromethyl)pyridin-2-yl)methanamine

Product 1

HCID 10927071HCID 10927071, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of (3-chloro-5-trifluoromethyl-2-pyridyl)methylamine (0.35 g) in dry ether (2 ml) was added to a solution of 2-trifluoromethylbenzoyl chloride (0.39 g) and triethylamine (0.27 ml) in dry ether (5 ml) and the mixture stirred overnight. Water (20 ml) and ethyl acetate (10 ml) were added and the organic phase was separated and washed with aqueous sodium hydrogen carbonate, dried and evaporated under reduced pressure. The residue was purified by silica gel chromatography to give the title product, m.p. 127-30° C.

Workup

  1. customthe organic phase was separated
  2. washwashed with aqueous sodium hydrogen carbonate
  3. customdried
  4. customevaporated under reduced pressure
  5. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-1fe9cf47223d4d429c137b6b5314f812
Source dataset
uspto-grants-2004_12
Patent number
US06828441B2

Reaction notes

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