Pyridine → 2-(Diaminomethyleneamino)-4-(6-methanesulfonylaminomethylpyridin-2-yl)thiazole

HRID 2379870Notes

Reaction equation

HRID 2379870 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[NH2:6][CH2:7][C:8]1[N:13]=[C:12]([C:14]2[N:15]=[C:16]([N:19]=[C:20]([NH2:22])[NH2:21])[S:17][CH:18]=2)[CH:11]=[CH:10][CH:9]=1.N1C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>ClCCl.O.C(OCC)(=O)C.O1CCCC1>[NH2:21][C:20](=[N:19][C:16]1[S:17][CH:18]=[C:14]([C:12]2[CH:11]=[CH:10][CH:9]=[C:8]([CH2:7][NH:6][S:2]([CH3:1])(=[O:4])=[O:3])[N:13]=2)[N:15]=1)[NH2:22]

Participants

9

Reactant 4

HCID 1049PyridineHCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chlorideHCID 103997684-(6-Aminomethylpyridin-2-yl)-2-(diaminomethyleneamino)thiazole

Product 1

HCID 103143032-(Diaminomethyleneamino)-4-(6-methanesulfonylaminomethylpyridin-2-yl)thiazole

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methanesulfonyl chloride (0.58 ml) was added a mixture of 4-(6-aminomethylpyridin-2-yl)-2-(diaminomethyleneamino)thiazole (1.8 g) and pyridine (0.81 ml) in dichloromethane (40 ml) under ice-cooling and the mixture was stirred for 23 hours at ambient temperature. The reaction mixture was added a mixture of tetrahydrofuran, ethyl acetate and water and the mixture was adjusted to pH 9.5 with 20% aqueous potassium carbonate. The separated organic layer was washed with brine, dried over magnesium sulfate and evaporated. The residue was recrystallized-from an aqueous methanol to give 2-(diaminomethyleneamino)-4-(6-methanesulfonylaminomethylpyridin-2-yl)thiazole (0.4 g).

Workup

  1. temperaturecooling
  2. additionThe reaction mixture was added
  3. washThe separated organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-68d99f81d2bf41bdab63f338d3179532
Source dataset
uspto-grants-1994_11
Patent number
US05364871

Reaction notes

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