Triethylamine → Pyridine-3-sulfonic acid [2-(3'-chloro-2,3,5,6-tetrahydro-[1,2']bipyrazinyl-4-yl)-ethyl]-methyl-amide

HRID 553492Notes

Reaction equation

HRID 553492 reaction equation
C(N(CC)CC)C.[Cl:8][C:9]1[C:10]([N:15]2[CH2:20][CH2:19][N:18]([CH2:21][CH2:22][NH:23][CH3:24])[CH2:17][CH2:16]2)=[N:11][CH:12]=[CH:13][N:14]=1.Cl.[N:26]1[CH:31]=[CH:30][CH:29]=[C:28]([S:32](Cl)(=[O:34])=[O:33])[CH:27]=1>ClCCl.C(=O)(O)[O-].[Na+]>[Cl:8][C:9]1[C:10]([N:15]2[CH2:16][CH2:17][N:18]([CH2:21][CH2:22][N:23]([CH3:24])[S:32]([C:28]3[CH:27]=[N:26][CH:31]=[CH:30][CH:29]=3)(=[O:34])=[O:33])[CH2:19][CH2:20]2)=[N:11][CH:12]=[CH:13][N:14]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 12571517Pyridine-3-sulfonyl chloride hydrochlorideHCID 59252197[2-(3'-Chloro-2,3,5,6-tetrahydro-[1,2']bipyrazinyl-4-yl)-ethyl]-methyl-amine

Product 1

HCID 86640207Pyridine-3-sulfonic acid [2-(3'-chloro-2,3,5,6-tetrahydro-[1,2']bipyrazinyl-4-yl)-ethyl]-methyl-amideYield 91%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

Add triethylamine (0.426 mL, 3.058 mmol) to a stirring solution of [2-(3′-chloro-2,3,5,6-tetrahydro-[1,2′]bipyrazinyl-4-yl)-ethyl]-methyl-amine (0.200 g, 0.612 mmol) in dichloromethane (5 mL). Add pyridine-3-sulfonyl chloride hydrochloride salt (0.157 g, 0.734 mmol) at room temperature. Stir at room temperature for 20 min. Dilute with dichloromethane and saturated aqueous sodium bicarbonate. Separate and extract the aqueous fraction with dichloromethane. Combine the organic fractions, dry over sodium sulfate, filter, and concentrate. Purify the resulting material by silica gel chromatography eluting with hexanes:acetone 4:1 to afford the title preparation (0.220 g, 91% yield). MS ES: m/z=397 [M+H]+.

Workup

  1. customat room temperature
  2. customSeparate
  3. extractionextract the aqueous fraction with dichloromethane
  4. dry with materialdry over sodium sulfate
  5. filtrationfilter
  6. concentrationconcentrate
  7. customPurify the resulting material by silica gel chromatography
  8. washeluting with hexanes:acetone 4:1
  9. customto afford the title
  10. custompreparation (0.220 g, 91% yield)

Sources & evidence

ORD record
ord-4ed4861aad2449d292aaa32126e8e5d1
Source dataset
uspto-grants-2011_11
Patent number
US08048884B2

Reaction notes

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