Triethylamine → 5-(2-chloro-pyridine-3-carbonyl)-1H-pyrrole-3-sulfonic acid (2-morpholin-4-yl-ethyl)-amide

HRID 456639Notes

Reaction equation

HRID 456639 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.[NH2:19][CH2:20][CH2:21][N:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1.C(N(CC)CC)C>C(Cl)Cl>[N:22]1([CH2:21][CH2:20][NH:19][S:15]([C:12]2[CH:11]=[C:10]([C:8]([C:7]3[C:2]([Cl:1])=[N:3][CH:4]=[CH:5][CH:6]=3)=[O:9])[NH:14][CH:13]=2)(=[O:17])=[O:16])[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 4082852-MorpholinoethylamineHCID 184368905-(2-chloro-pyridine-3-carbonyl)-1H-pyrrole-3-sulfonyl chloride

Product 1

HCID 865922425-(2-chloro-pyridine-3-carbonyl)-1H-pyrrole-3-sulfonic acid (2-morpholin-4-yl-ethyl)-amideYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-(2-chloro-pyridine-3-carbonyl)-1H-pyrrole-3-sulfonyl chloride (500 mg, 1.64 mmol) in DCM (5 mL) was added 4-(2-aminoethyl)morpholine (427 mg, 3.28 mmol) and triethylamine (0.5 mL). The mixture was stirred at room temperature for 4 hours. The reaction was extracted with DCM, the combined DCM was washed with water and brine, dried and concentrated. The residue was purified on a silica gel column to give 450 mg (69%) of 5-(2-chloro-pyridine-3-carbonyl)-1H-pyrrole-3-sulfonic acid (2-morpholin-4-yl-ethyl)-amide as a white solid.

Workup

  1. extractionThe reaction was extracted with DCM
  2. washthe combined DCM was washed with water and brine
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified on a silica gel column

Sources & evidence

ORD record
ord-ea8273e4e1e4432cbdb553f3434c91dc
Source dataset
uspto-grants-2007_03
Patent number
US07186716B2

Reaction notes

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