Triethylamine → HCID 68304437, compound

HRID 1846679Notes

Reaction equation

HRID 1846679 reaction equation
[CH2:1]([O:3][C:4](=[O:23])[CH2:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[C:17]([NH2:18])=[CH:16][CH:15]=[C:14]([C:19]([F:22])([F:21])[F:20])[N:13]=2)[CH2:8][CH2:7]1)[CH3:2].C(N(CC)CC)C.[Cl:31][C:32]1[CH:33]=[C:34]([CH:38]=[CH:39][CH:40]=1)[C:35](Cl)=[O:36]>C(#N)C>[CH2:1]([O:3][C:4](=[O:23])[CH2:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[C:17]([NH:18][C:35](=[O:36])[C:34]3[CH:38]=[CH:39][CH:40]=[C:32]([Cl:31])[CH:33]=3)=[CH:16][CH:15]=[C:14]([C:19]([F:21])([F:22])[F:20])[N:13]=2)[CH2:8][CH2:7]1)[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 69252Benzoyl chloride, 3-chloro-2×HCID 68304438HCID 68304438, compound

Product 1

HCID 68304437HCID 68304437, compoundYield 108.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of 0.150 g (0.453 mmol) of (3′-amino-6′-trifluoromethyl-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-yl)-acetic acid ethyl ester in acetonitrile (3 mL) is added 0.19 mL (1.4 mmol) of triethylamine followed by 0.069 mL (0.54 mmol) of 3-chlorobenzoyl chloride. The mixture is stirred overnight at room temperature then an additional 0.21 mL (1.6 mmol) of 3-chlorobenzoyl chloride is added and the mixture is stirred for an additional two days. The mixture is concentrated under reduced pressure and purified by flash silica gel chromatography to provide 0.23 g (quant.) of [3′-(3-chloro-benzoylamino)-6′-trifluoromethyl-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-yl]-acetic acid ethyl ester.

Workup

  1. stirringthe mixture is stirred for an additional two days
  2. concentrationThe mixture is concentrated under reduced pressure
  3. custompurified by flash silica gel chromatography

Sources & evidence

ORD record
ord-96c9b1f48b594b18a69e84d71600a03c
Source dataset
uspto-grants-2015_02
Patent number
US08952004B2

Reaction notes

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