Ethylmorpholine → N-(4-cyanomethyl-1H-indazol-7-yl)methanesulfonamide

HRID 1032547Notes

Reaction equation

HRID 1032547 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:11][C:12]#[N:13])=[C:6]2[C:10]=1[NH:9][N:8]=[CH:7]2.[CH3:14][S:15](Cl)(=[O:17])=[O:16].C(N1CCOCC1)C>CN(C)C=O.O1CCCC1>[C:12]([CH2:11][C:5]1[CH:4]=[CH:3][C:2]([NH:1][S:15]([CH3:14])(=[O:17])=[O:16])=[C:10]2[C:6]=1[CH:7]=[N:8][NH:9]2)#[N:13]

Participants

6

Reactant 3

HCID 7525EthylmorpholineHCID 31297Methanesulfonyl chlorideHCID 193544342-(7-amino-1H-indazol-4-yl)acetonitrile

Product 1

HCID 22166017N-(4-cyanomethyl-1H-indazol-7-yl)methanesulfonamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

At 0° C., 1.7 g of 2-(7-amino-1H-indazol-4-yl)acetonitrile in 15 ml of dimethylformamide and 5 ml of tetrahydrofuran is combined with 0.96 ml of methanesulfonyl chloride and 1.56 ml of N-ethylmorpholine and agitated for 16 hours at room temperature. The mixture is concentrated, chromatographed over silica gel with methanol/dichloromethane (1:3), and recrystallized from methanol, thus producing 2.2 g of N-(4-cyanomethyl-1H-indazol-7-yl)methanesulfonamide, mp 223°-225° C.

Workup

  1. customAt 0° C.
  2. concentrationThe mixture is concentrated
  3. customchromatographed over silica gel with methanol/dichloromethane (1:3)
  4. customrecrystallized from methanol

Sources & evidence

ORD record
ord-d554e39a32904f1b8574b3b62861c667
Source dataset
uspto-grants-1990_09
Patent number
US04958026

Reaction notes

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