Benzoyl chloride, 3-chloro- → HCID 67343888, compound

HRID 1846630Notes

Reaction equation

HRID 1846630 reaction equation
[C:1]([O:5][C:6](=[O:26])[NH:7][CH2:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]2[C:20]([NH2:21])=[CH:19][C:18]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:17][N:16]=2)[CH2:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)C(C)C)(C)C.[Cl:36][C:37]1[CH:38]=[C:39]([CH:43]=[CH:44][CH:45]=1)[C:40](Cl)=[O:41]>C(Cl)Cl.C(OCC)(=O)C>[C:1]([O:5][C:6](=[O:26])[NH:7][CH2:8][CH:9]1[CH2:10][CH2:11][N:12]([C:15]2[C:20]([NH:21][C:40](=[O:41])[C:39]3[CH:43]=[CH:44][CH:45]=[C:37]([Cl:36])[CH:38]=3)=[CH:19][C:18]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:17][N:16]=2)[CH2:13][CH2:14]1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 69252Benzoyl chloride, 3-chloro-2×HCID 81531Diisopropylethylamine2×HCID 71238524HCID 71238524, compound

Product 1

HCID 67343888HCID 67343888, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 0.300 g (0.780 mmol) of (3′-amino-5′-methanesulfonyl-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-ylmethyl)-carbamic acid tert-butyl ester in methylene chloride (3 mL) under argon, cooled to 0° C., is added 0.136 mL (0.780 mmol) of N,N-diisopropylethylamine followed by 0.110 mL (0.858 mmol) of 3-chlorobenzoyl chloride. The mixture is stirred at 0° C. for 15 min then warmed to room temperature and stirred for 2 days during which time the solvent evaporates. The residue is dissolved in methylene chloride (3 mL) and an additional 0.136 mL (0.780 mmol) of N,N-diisopropylethylamine and 0.110 mL (0.858 mmol) of 3-chlorobenzoyl chloride is added. The reaction is stirred overnight at room temperature. The mixture is diluted with ethyl acetate and washed with water followed by aqueous ammonium chloride and then aqueous sodium carbonate. The organic phase is dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue is purified by preparative thin layer chromatography to give 0.186 g (46.0%) of [3′-(3-chloro-benzoylamino)-5′-methanesulfonyl-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-ylmethyl]-carbamic acid tert-butyl ester as a beige foam.

Workup

  1. temperaturethen warmed to room temperature
  2. stirringstirred for 2 days during which time the solvent
  3. customevaporates
  4. dissolutionThe residue is dissolved in methylene chloride (3 mL)
  5. stirringThe reaction is stirred overnight at room temperature
  6. washwashed with water
  7. dry with materialThe organic phase is dried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue is purified by preparative thin layer chromatography

Sources & evidence

ORD record
ord-740cd445eb7e40e1b85caa90247d2afd
Source dataset
uspto-grants-2015_02
Patent number
US08952004B2

Reaction notes

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