Diisopropylethylamine → US10385022, Example 6

HRID 877964Notes

Reaction equation

HRID 877964 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1)[C:5](Cl)=[O:6].[CH3:15][NH:16][C:17]1[CH:18]=[N:19][CH:20]=[CH:21][C:22]=1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[CH3:29].CCN(C(C)C)C(C)C>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1)[C:5]([N:16]([CH3:15])[C:17]1[CH:18]=[N:19][CH:20]=[CH:21][C:22]=1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[CH3:29])=[O:6]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 5193643-Fluoro-5-(trifluoromethyl)benzoyl chlorideHCID 18403336N-methyl-4-o-tolylpyridin-3-amine

Product 1

HCID 60197094US10385022, Example 6Yield 57%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Fluoro-5-trifluoromethylbenzoyl chloride (92 mg, 0.41 mmol, CAS RN 171243-30-4) was added to a solution of methyl-(4-o-tolyl-pyridin-3-yl)-amine (40 mg, 0.20 mmol, example 1, intermediate a) and DIPEA (70 μL, 0.40 mmol) in THF (1 mL). After 2 h, an additional 25 μL of acyl chloride was added. The reaction mixture was stirred overnight, filtered and all volatiles removed. The resulting oil was purified by flash chromatography on silica gel eluting with 33-50% EtOAc in n-hexane to yield the product as a waxy solid (45 mg, 57%). MS (ESI): m/z=470.0 [M+H]+.

Workup

  1. filtrationfiltered
  2. customall volatiles removed
  3. customThe resulting oil was purified by flash chromatography on silica gel eluting with 33-50% EtOAc in n-hexane

Sources & evidence

ORD record
ord-af7b6bb4788242359edbb2b600642689
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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