2-Chloro-3-isothiocyanatopyridine → Methyl 4-(5-bromo-2-(thiazolo[5,4-b]pyridin-2-ylamino)pyridin-3-ylthio)benzoate hydrochloride

HRID 335187Notes

Reaction equation

HRID 335187 reaction equation
[NH2:1][C:2]1[C:7]([S:8][C:9]2[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][CH:10]=2)=[CH:6][C:5]([Br:19])=[CH:4][N:3]=1.[Cl:20][C:21]1[C:26]([N:27]=[C:28]=[S:29])=[CH:25][CH:24]=[CH:23][N:22]=1>CN(C=O)C.ClCCl>[ClH:20].[Br:19][C:5]1[CH:6]=[C:7]([S:8][C:9]2[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][CH:10]=2)[C:2]([NH:1][C:28]2[S:29][C:21]3[C:26]([N:27]=2)=[CH:25][CH:24]=[CH:23][N:22]=3)=[N:3][CH:4]=1

Participants

5

Reactant 2

HCID 128680882-Chloro-3-isothiocyanatopyridineHCID 66994425Methyl 4-(2-amino-5-bromopyridin-3-ylthio)benzoate

Product 1

HCID 86631508Methyl 4-(5-bromo-2-(thiazolo[5,4-b]pyridin-2-ylamino)pyridin-3-ylthio)benzoate hydrochlorideYield 41.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

Added methyl 4-(2-amino-5-bromopyridin-3-ylthio)benzoate (1.00 g, 2.95 mmol) to a mixture of 2-chloro-3-isothiocyanatopyridine (0.503 g, 2.95 mmol) in DMF (4 mL). Stirred at 80° C. for an hour, then at 110° C. for 2 hours. Cooled, diluted with dichloromethane (8 mL), filtered, washed with dichloromethane, and dried to afford the title compound (0.625 g, 41.6% yield). 1H NMR (ds-DMSO) δ 3.84 (s, 3H), 7.40 (dd, 1H), 7.45 (d, 2H), 7.72 (d, 1H), 7.79 (bs, 1H), 7.96 (d, 2H), 8.34 (d, 1H), 8.56 (s, 1H).

Workup

  1. temperatureCooled
  2. filtrationfiltered
  3. washwashed with dichloromethane
  4. customdried

Sources & evidence

ORD record
ord-2dba8e12e3d440778c728183574e5a56
Source dataset
uspto-grants-2014_11
Patent number
US08883828B2

Reaction notes

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