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

HRID 553488Notes

Reaction equation

HRID 553488 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.[CH3:25][N:26]1[CH:30]=[C:29]([S:31](Cl)(=[O:33])=[O:32])[CH:28]=[N: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:31]([C:29]3[CH:28]=[N:27][N:26]([CH3:25])[CH:30]=3)(=[O:33])=[O:32])[CH2:19][CH2:20]2)=[N:11][CH:12]=[CH:13][N:14]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 170247301-methyl-1H-pyrazole-4-sulfonyl chlorideHCID 59252197[2-(3'-Chloro-2,3,5,6-tetrahydro-[1,2']bipyrazinyl-4-yl)-ethyl]-methyl-amine

Product 1

HCID 866402031-Methyl-1H-pyrazole-4-sulfonic acid [2-(3'-chloro-2,3,5,6-tetrahydro-[1,2']bipyrazinyl-4-yl)-ethyl]-methyl-amideYield 84%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

Add triethylamine (0.852 mL, 6.116 mmol) to a stirring solution of [2-(3′-chloro-2,3,5,6-tetrahydro-[1,2′]bipyrazinyl-4-yl)-ethyl]-methyl-amine (0.500 g, 1.529 mmol) in dichloromethane (10 mL). Add 1-methyl-1H-pyrazole-4-sulfonyl chloride (0.331 g, 1.834 mmol) at room temperature. Stir at room temperature for 18 hr. Dilute with dichloromethane and saturated aqueous sodium bicarbonate. Separate and extract the aqueous layer with dichloromethane. Combine the organic layers, dry over sodium sulfate, filter, and concentrate. Purify the resulting material by silica gel chromatography eluting with hexanes:acetone 6:4 to 4:6 to afford the title preparation (0.514 g, 84% yield). MS ES: m/z=400 [M+H]+.

Workup

  1. customat room temperature
  2. customSeparate
  3. extractionextract the aqueous layer 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 6:4 to 4:6
  9. customto afford the title
  10. custompreparation (0.514 g, 84% yield)

Sources & evidence

ORD record
ord-2c76010d2f3f43b5b2a64e93188887b3
Source dataset
uspto-grants-2011_11
Patent number
US08048884B2

Reaction notes

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