Benzoyl chloride, 3-chloro- → HCID 68304201, compound

HRID 1846684Notes

Reaction equation

HRID 1846684 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]([S:19]([CH3:22])(=[O:21])=[O:20])[N:13]=2)[CH2:8][CH2:7]1)[CH3:2].C(N(CC)C(C)C)(C)C.[Cl:33][C:34]1[CH:35]=[C:36]([CH:40]=[CH:41][CH:42]=1)[C:37](Cl)=[O:38]>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:37](=[O:38])[C:36]3[CH:40]=[CH:41][CH:42]=[C:34]([Cl:33])[CH:35]=3)=[CH:16][CH:15]=[C:14]([S:19]([CH3:22])(=[O:21])=[O:20])[N:13]=2)[CH2:8][CH2:7]1)[CH3:2]

Participants

5

Reactant 3

HCID 69252Benzoyl chloride, 3-chloro-2×HCID 81531DiisopropylethylamineHCID 68304200HCID 68304200, compound

Product 1

HCID 68304201HCID 68304201, compoundYield 49.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of 0.080 g (0.23 mmol) of (3′-amino-6′-methanesulfonyl-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-yl)-acetic acid ethyl ester in acetonitrile (5 mL) is added 0.12 mL (0.70 mmol) of N,N-diisopropylethylamine followed by 0.032 mL (0.28 mmol) of 3-chlorobenzoyl chloride. The mixture is heated at 80° C. for 1 h then an additional 0.096 mL (0.84 mmol) of 3-chlorobenzoyl chloride is added. The mixture is stirred at 80° C. for an additional 10 minutes then cooled to room temperature and concentrated under reduced pressure. The residue is purified by flash silica gel chromatography to provide 0.055 g (49%) of [3′-(3-chloro-benzoylamino)-6′-methanesulfonyl-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-yl]-acetic acid ethyl ester as a colorless foam.

Workup

  1. temperaturethen cooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. customThe residue is purified by flash silica gel chromatography

Sources & evidence

ORD record
ord-c4739e3ebef34b74a6b7c744f75cae90
Source dataset
uspto-grants-2015_02
Patent number
US08952004B2

Reaction notes

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