Methanesulfonyl chloride → HCID 178481754, compound

HRID 1628060Notes

Reaction equation

HRID 1628060 reaction equation
[CH3:1][N:2]1[C:6]2=[C:7]3[CH:13]=[C:12]([C:14]4[CH:15]=[C:16]([CH2:20][NH2:21])[CH:17]=[CH:18][CH:19]=4)[NH:11][C:8]3=[N:9][CH:10]=[C:5]2[CH:4]=[N:3]1.CCN(C(C)C)C(C)C.[CH3:31][S:32](Cl)(=[O:34])=[O:33]>CN(C=O)C>[CH3:1][N:2]1[C:6]2=[C:7]3[CH:13]=[C:12]([C:14]4[CH:15]=[C:16]([CH:17]=[CH:18][CH:19]=4)[CH2:20][NH:21][S:32]([CH3:31])(=[O:34])=[O:33])[NH:11][C:8]3=[N:9][CH:10]=[C:5]2[CH:4]=[N:3]1

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 178481753HCID 178481753, compound

Product 1

HCID 178481754HCID 178481754, compoundYield 59.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a flask was added (3-(1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-7-yl)phenyl)methanamine (0.075 g, 0.27 mmol, Example #T.3.1), DMF (2.7 mL), DIEA (0.118 mL, 0.676 mmol) and MsCl (0.025 mL, 0.325 mmol). The mixture was stirred at rt for about 10 min. The mixture was purified directly by flash chromatography (25 g silica gel column, DCM/MeOH 1:0 to 10:1 with 2% 2.0 M NH3 in EtOH). The solid was dried under reduced pressure at about 60° C. for about 1 h to give N-(3-(1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-7-yl)benzyl)methanesulfonamide (0.057 g, 58%): LC/MS (Table 2, Method a) Rt=1.84 min; MS m/z 356 (M+H)+. Syk IC50=B.

Workup

  1. customThe mixture was purified directly by flash chromatography (25 g silica gel column, DCM/MeOH 1:0 to 10:1 with 2% 2.0 M NH3 in EtOH)
  2. customThe solid was dried under reduced pressure at about 60° C. for about 1 h

Sources & evidence

ORD record
ord-839c7e4714754de6a7355e9c4add6d6a
Source dataset
uspto-grants-2014_07
Patent number
US08785639B2

Reaction notes

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