Pyridine → HCID 69360208, compound

HRID 852566Notes

Reaction equation

HRID 852566 reaction equation
[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:18]=[C:17]([NH2:19])[CH:16]=[C:6]([C:7]([N:9]([CH2:13][CH2:14][CH3:15])[CH2:10][CH2:11][CH3:12])=[O:8])[CH:5]=1.N1C=CC=CC=1.[Cl:27][CH2:28][CH2:29][CH2:30][S:31](Cl)(=[O:33])=[O:32]>CN(C1C=CN=CC=1)C.C(Cl)Cl.CCOC(C)=O>[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:18]=[C:17]([NH:19][S:31]([CH2:30][CH2:29][CH2:28][Cl:27])(=[O:33])=[O:32])[CH:16]=[C:6]([C:7]([N:9]([CH2:10][CH2:11][CH3:12])[CH2:13][CH2:14][CH3:15])=[O:8])[CH:5]=1

Participants

7

Reactant 3

HCID 1049PyridineHCID 154103-Chloropropanesulphonyl chlorideHCID 22593627Methyl 3-amino-5-[(dipropylamino)carbonyl]Benzoate

Product 1

HCID 69360208HCID 69360208, compoundYield 86%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 5-amino-N,N-dipropyl-isophthalamic acid methyl ester (D88) (1.4 g, 5.0 mmol, 1 equiv), DMAP (100 mg) and pyridine (392 mg, 5.0 mmol, 1.1 equiv) in CH2Cl2 (20 ml) was treated dropwise with 3-chloropropane-1-sulfonyl chloride (946 mg, 5.3 mmol, 1.1 equiv). The resulting mixture was stirred for 16 h at room temperature and then diluted with AcOEt (100 ml). The resulting solution was washed with 2N aqueous HCl solution (50 ml) followed by saturated aqueous NaHCO3 solution (50 ml), dried over MgSO4 and concentrated in vacuo. The residue was triturated with Et2O to give 5-(3-chloro-propane-1-sulfonylamino)-N,N-dipropyl-isophthalamic acid methyl ester (D91) (1.8 g, 86%) as a pink solid.

Workup

  1. washThe resulting solution was washed with 2N aqueous HCl solution (50 ml)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was triturated with Et2O

Sources & evidence

ORD record
ord-6f703d9f32f94f8788247f453c4adbd4
Source dataset
uspto-grants-2007_08
Patent number
US07253198B2

Reaction notes

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