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Methanesulfonyl chloride → 6-(3-(2,4-Difluorophenyl)-1-(1-(methylsulfonyl)pyrrolidin-3-yl)-1H-pyrazol-4-yl)-3-isopropyl-[1,2,4]triazolo[4,3-b]pyridazine

HRID 1929999
Notes
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Reaction equation

HRID 1929999 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:13]([C:14]2[CH:15]=[CH:16][C:17]3[N:18]([C:20]([CH:23]([CH3:25])[CH3:24])=[N:21][N:22]=3)[N:19]=2)=[CH:12][N:11]([CH:26]2[CH2:30][CH2:29][NH:28][CH2:27]2)[N:10]=1.CCN(C(C)C)C(C)C.[CH3:40][S:41](Cl)(=[O:43])=[O:42]>C(Cl)Cl>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:13]([C:14]2[CH:15]=[CH:16][C:17]3[N:18]([C:20]([CH:23]([CH3:24])[CH3:25])=[N:21][N:22]=3)[N:19]=2)=[CH:12][N:11]([CH:26]2[CH2:30][CH2:29][N:28]([S:41]([CH3:40])(=[O:43])=[O:42])[CH2:27]2)[N:10]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 579298656-(3-(2,4-Difluorophenyl)-1-(pyrrolidin-3-yl)-1H-pyrazol-4-yl)-3-isopropyl-[1,2,4]triazolo[4,3-b]pyridazine

Product 1

HCID 579298546-(3-(2,4-Difluorophenyl)-1-(1-(methylsulfonyl)pyrrolidin-3-yl)-1H-pyrazol-4-yl)-3-isopropyl-[1,2,4]triazolo[4,3-b]pyridazineYield 96.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a round bottom flask was added 6-(3-(2,4-difluorophenyl)-1-(pyrrolidin-3-yl)-1H-pyrazol-4-yl)-3-isopropyl-[1,2,4]triazolo[4,3-b]pyridazine (0.105 g, 0.256 mmol, Example #Q.1.1.1), DCM (5 mL) and DIPEA (0.054 mL, 0.31 mmol). Then methanesulfonyl chloride (0.020 mL, 0.26 mmol) was added. The reaction mixture was stirred at ambient temperature for about 10 min. The reaction mixture was purified directly by flash chromatography (40 g RediSep® silica gel; DCM/MeOH gradient from 1:0 to 9:1) to give the title compound (0.120 g, 96%): LC/MS (Table 1, Method g) Rt=2.28 min; MS m/z: 488.3 (M+H)+.

Workup

  1. customThe reaction mixture was purified directly by flash chromatography (40 g RediSep® silica gel; DCM/MeOH gradient from 1:0 to 9:1)

Sources & evidence

ORD record
ord-b19d4fb0c81d4b93b7997210ed03832b
Source dataset
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08188083B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes