Triethylamine → HCID 86640204, compound

HRID 553489Notes

Reaction equation

HRID 553489 reaction equation
C(N(CC)CC)C.[OH:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[C:17]([N:22]3[CH2:27][CH2:26][N:25]([CH2:28][CH2:29][N:30]([CH3:40])[S:31]([C:34]4[CH:35]=[N:36][N:37]([CH3:39])[CH:38]=4)(=[O:33])=[O:32])[CH2:24][CH2:23]3)=[N:18][CH:19]=[CH:20][N:21]=2)=[CH:12][CH:11]=1.[CH3:41][S:42](Cl)(=[O:44])=[O:43]>ClCCl.[Cl-].[Na+].O>[CH3:40][N:30]([S:31]([C:34]1[CH:35]=[N:36][N:37]([CH3:39])[CH:38]=1)(=[O:33])=[O:32])[CH2:29][CH2:28][N:25]1[CH2:24][CH2:23][N:22]([C:17]2[C:16]([C:13]3[CH:14]=[CH:15][C:10]([CH2:9][O:8][S:42]([CH3:41])(=[O:44])=[O:43])=[CH:11][CH:12]=3)=[N:21][CH:20]=[CH:19][N:18]=2)[CH2:27][CH2:26]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 25211790HCID 25211790, compound

Product 1

HCID 86640204HCID 86640204, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

Add triethylamine (0.653 mmol, 0.091 mL) to a stirred solution of 1-methyl-1H-pyrazole-4-sulfonic acid {2-[3′-(4-hydroxymethyl-phenyl)-2,3,5,6-tetrahydro-[1,2′]bipyrazinyl-4-yl]-ethyl}-methyl-amide (0.594 mmol, 0.280 g) in dry dichloromethane (5 mL) at room temperature under nitrogen. Add methanesulfonyl chloride (0.653 mmol, 0.051 mL). Allow the mixture to warm to room temperature and stir 1 hr. Dilute with dichloromethane and brine. Separate and extract the aqueous phase with dichloromethane. Combine organics, dry over Na2SO4, and concentrate to dryness to afford the title preparation (0.330 g, crude). The material is used without further purification. MS ES: m/z=550 [M+H]+.

Workup

  1. customSeparate
  2. extractionextract the aqueous phase with dichloromethane
  3. dry with materialCombine organics, dry over Na2SO4
  4. concentrationconcentrate to dryness
  5. customto afford the title
  6. custompreparation (0.330 g, crude)
  7. customThe material is used without further purification

Sources & evidence

ORD record
ord-d2a98b93bba34d268b2f640621c016b9
Source dataset
uspto-grants-2011_11
Patent number
US08048884B2

Reaction notes

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