Methanesulfonamide → HCID 178480011, compound

HRID 1628120Notes

Reaction equation

HRID 1628120 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11](O)=[O:12])=[CH:8][CH:9]=2)[C:4]([C:14]2[NH:26][C:17]3=[N:18][CH:19]=[C:20]4[CH:24]=[N:23][N:22]([CH3:25])[C:21]4=[C:16]3[CH:15]=2)=[CH:3]1.[CH3:27][S:28]([NH2:31])(=[O:30])=[O:29]>ClCCCl.CC(O)(C)C.CN(C1C=CN=CC=1)C>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([NH:31][S:28]([CH3:27])(=[O:30])=[O:29])=[O:12])=[CH:8][CH:9]=2)[C:4]([C:14]2[NH:26][C:17]3=[N:18][CH:19]=[C:20]4[CH:24]=[N:23][N:22]([CH3:25])[C:21]4=[C:16]3[CH:15]=2)=[CH:3]1

Participants

6

Reactant 2

HCID 72879MethanesulfonamideHCID 178480012HCID 178480012, compound

Product 1

HCID 178480011HCID 178480011, compoundYield 42%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 111,2-DichloroethaneSolvent2×HCID 6386tert-ButanolSolvent

Procedure

1-Methyl-3-(1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-7-yl)-1H-indole-5-carboxylic acid (0.047 g, 0.14 mmol, Example #AN.1), methanesulfonamide (0.039 g, 0.41 mmol) and EDC (0.065 g, 0.34 mmol) were combined in a mixture of DCE (1.31 mL) and t-BuOH (1.31 mL). DMAP (0.050 g, 0.41 mmol) was added and the mixture was stirred at rt for about 16 h. The mixture was purified by flash chromatography (12 g silica gel column, (6:3:1 CHCl3/MeOH/saturated NH4OH)/EtOAc 50-85%) to give 1-methyl-3-(1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-7-yl)-N-(methylsulfonyl)-1H-indole-5-carboxamide (0.024 g, 42%): LC/MS (Table 2, Method a) Rt=1.55 min; MS m/z 423 (M+H)+. Syk IC50=A.

Workup

  1. customThe mixture was purified by flash chromatography (12 g silica gel column, (6:3:1 CHCl3/MeOH/saturated NH4OH)/EtOAc 50-85%)

Sources & evidence

ORD record
ord-4f11ef64ae2f432ca295e2370215ee93
Source dataset
uspto-grants-2014_07
Patent number
US08785639B2

Reaction notes

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