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Triethylamine → Methanesulfonic acid 6-[3-(5-Methylisoxazol-3-yl)-[1,2,4]triazolo[3,4-alpha]-phthalazin-6-yloxymethyl]pyridin-3-ylmethyl ester

HRID 2183496
Notes
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Reaction equation

HRID 2183496 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH3:6][C:7]1[O:11][N:10]=[C:9]([C:12]2[N:16]3[N:17]=[C:18]([O:25][CH2:26][C:27]4[N:32]=[CH:31][C:30]([CH2:33][OH:34])=[CH:29][CH:28]=4)[C:19]4[C:24]([C:15]3=[N:14][N:13]=2)=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH:8]=1.CCN(CC)CC>C(Cl)Cl>[CH3:6][C:7]1[O:11][N:10]=[C:9]([C:12]2[N:16]3[N:17]=[C:18]([O:25][CH2:26][C:27]4[N:32]=[CH:31][C:30]([CH2:33][O:34][S:2]([CH3:1])(=[O:4])=[O:3])=[CH:29][CH:28]=4)[C:19]4[C:24]([C:15]3=[N:14][N:13]=2)=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH:8]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 131724934{6-[3-(5-Methylisoxazol-3-yl)-[1,2,4]triazolo[3,4-alpha]phthalazin-6-yloxymethyl]pyridin-3-yl}methanol

Product 1

HCID 131724935Methanesulfonic acid 6-[3-(5-Methylisoxazol-3-yl)-[1,2,4]triazolo[3,4-alpha]-phthalazin-6-yloxymethyl]pyridin-3-ylmethyl ester

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent
2×

Procedure

Methanesulfonyl chloride (1.07 ml, 13.9 mmol) was added to a stirred suspension of {6-[3-(5-methylisoxazol-3-yl)-[1,2,4]triazolo[3,4-α]phthalazin-6-yloxymethyl]pyridin-3-yl}methanol (2.78 mmol), Et3N (1.94 ml, 13.9 mmol) in CH2Cl2 (100 ml) under nitrogen. The reaction mixture was stirred overnight and then diluted with CH2Cl2. The resulting solution was washed with H2O (100 ml), 1 N HCl (100 ml), NaHCO3 (sat., 100 ml) and brine (100 ml). The solution was then dried MgSO4) and concentrated under reduced pressure. The resultant mesylate was used without further purification.

Workup

  1. washThe resulting solution was washed with H2O (100 ml), 1 N HCl (100 ml), NaHCO3 (sat., 100 ml) and brine (100 ml)
  2. concentrationdried MgSO4) and concentrated under reduced pressure
  3. customThe resultant mesylate was used without further purification

Sources & evidence

ORD record
ord-389b86a5bb6049b69e8581c4c7b175e0
Source dataset
uspto-grants-2005_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06900209B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes