Hydrochloric Acid → N-[5-Methyl-2-(2-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-phenyl]-methanesulfonamide

HRID 1262352Notes

Reaction equation

HRID 1262352 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:9]2[N:17]3[C:12]([CH:13]=[N:14][C:15]([S:18][CH3:19])=[N:16]3)=[CH:11][CH:10]=2)=[C:6]([NH2:8])[CH:7]=1.N1C=CC=CC=1.[CH3:26][S:27](Cl)(=[O:29])=[O:28].Cl>>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:9]2[N:17]3[C:12]([CH:13]=[N:14][C:15]([S:18][CH3:19])=[N:16]3)=[CH:11][CH:10]=2)=[C:6]([NH:8][S:27]([CH3:26])(=[O:29])=[O:28])[CH:7]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 667127275-Methyl-2-(2-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-phenylamine

Product 1

HCID 66712100N-[5-Methyl-2-(2-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-phenyl]-methanesulfonamide

Procedure

To a mixture of 5-Methyl-2-(2-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-phenylamine (480 mg, 1.8 mmol) in dry pyridine (4 mL, 50 mmol) was added at 0° C. methanesulfonyl chloride (160 uL, 2.1 mmol). The mixture was stirred for 2 h and was thrown to 3N HCl. The mixture was extracted from EtOAc. Combined organic was washed with brine and was dried. After solvent evaporation, the product, N-[5-Methyl-2-(2-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-phenyl]-methanesulfonamide, was obtained as a yellow solid (591 mg, 96%). The solid was used directly for the next step.

Workup

  1. extractionThe mixture was extracted from EtOAc
  2. washCombined organic was washed with brine
  3. customwas dried
  4. customAfter solvent evaporation

Sources & evidence

ORD record
ord-6fec2b9e34bf4bd0a412f0a4ff834060
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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