2,6-Dichlorobenzoyl chloride → HCID 69143447, compound

HRID 1348945Notes

Reaction equation

HRID 1348945 reaction equation
[CH3:1][O:2][C:3](=[O:27])[CH:4]([NH2:26])[CH2:5][C:6]1[CH:15]=[C:14]2[C:9]([CH2:10][CH2:11][N:12]([C:16](=[O:25])[C:17]3[C:22]([Cl:23])=[CH:21][CH:20]=[CH:19][C:18]=3[Cl:24])[CH2:13]2)=[CH:8][CH:7]=1.[Cl:28][C:29]1[CH:37]=[CH:36][CH:35]=[C:34]([Cl:38])[C:30]=1[C:31](Cl)=[O:32]>N1C=CC=CC=1>[CH3:1][O:2][C:3](=[O:27])[CH:4]([NH:26][C:31](=[O:32])[C:30]1[C:29]([Cl:28])=[CH:37][CH:36]=[CH:35][C:34]=1[Cl:38])[CH2:5][C:6]1[CH:15]=[C:14]2[C:9]([CH2:10][CH2:11][N:12]([C:16](=[O:25])[C:17]3[C:18]([Cl:24])=[CH:19][CH:20]=[CH:21][C:22]=3[Cl:23])[CH2:13]2)=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 783922,6-Dichlorobenzoyl chlorideHCID 69143130HCID 69143130, compound

Product 1

HCID 69143447HCID 69143447, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A stirred solution of 2-amino-3-[2-(2,6-dichloro-benzoyl]-1,2,3,4-tetrahydro-isoquinolin-7-yl]-propionic acid methyl ester (1.18 g, Reference Example 10) in dry pyridine (50 mL), under nitrogen and at room temperature, was treated dropwise with 2,6-dichloro-benzoyl chloride (0.67 g). The mixture was stirred at room temperature for 25 minutes and then at 65° C. for 40 minutes. The resulting dark red solution was cooled to room temperature and then evaporated. The residual red oil was dissolved in dichloromethane and this solution was washed with aqueous sodium bicarbonate solution (5%), then with water, then dried over magnesium sulfate and then evaporated. The residue was coated onto silica (8.5 g) using dichloromethane and then subjected to flash chromatography on silica eluting with a mixture of ethyl acetate and heptane (1:1, v/v) to give the title compound.

Workup

  1. waitat 65° C. for 40 minutes
  2. temperatureThe resulting dark red solution was cooled to room temperature
  3. customevaporated
  4. dissolutionThe residual red oil was dissolved in dichloromethane
  5. washthis solution was washed with aqueous sodium bicarbonate solution (5%)
  6. dry with materialwith water, then dried over magnesium sulfate
  7. customevaporated
  8. additionsubjected to flash chromatography on silica eluting with a mixture of ethyl acetate and heptane (1:1

Sources & evidence

ORD record
ord-29f27f31492f4440807bc3853389c46e
Source dataset
uspto-grants-2007_05
Patent number
US07211586B2

Reaction notes

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