Benzylamine → 5-(2-chloro-pyridine-3-carbonyl)1H-pyrrole-3-sulfonic acid benzylamide

HRID 456641Notes

Reaction equation

HRID 456641 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([C:10]2[NH:14][CH:13]=[C:12]([S:15](Cl)(=[O:17])=[O:16])[CH:11]=2)=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH2:19]([NH2:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(N(CC)CC)C>C(Cl)Cl>[CH2:19]([NH:26][S:15]([C:12]1[CH:11]=[C:10]([C:8]([C:7]2[C:2]([Cl:1])=[N:3][CH:4]=[CH:5][CH:6]=2)=[O:9])[NH:14][CH:13]=1)(=[O:17])=[O:16])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 8471TriethylamineHCID 184368905-(2-chloro-pyridine-3-carbonyl)-1H-pyrrole-3-sulfonyl chloride

Product 1

HCID 865922435-(2-chloro-pyridine-3-carbonyl)1H-pyrrole-3-sulfonic acid benzylamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 5-(2-chloro-pyridine-3-carbonyl)-1H-pyrrole-3-sulfonyl chloride (500 mg, 1.64 mmol) (from Example 17), benzylamine (351.5 mg, 3.28 mmol) and triethylamine (1 mL) in DCM (5 mL) was stirred at room temperature for 4 hours. The reaction was diluted with DCM, washed with water, dried and concentrated. The residue was purified on a silica gel column to give 5-(2-chloro-pyridine-3-carbonyl)1H-pyrrole-3-sulfonic acid benzylamide.

Workup

  1. washwashed with water
  2. customdried
  3. concentrationconcentrated
  4. customThe residue was purified on a silica gel column

Sources & evidence

ORD record
ord-ef087c159f7447888d65539c2c521c83
Source dataset
uspto-grants-2007_03
Patent number
US07186716B2

Reaction notes

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