Dimethylformamide → N-(5-bromo-3-(phenylthio)pyridin-2-yl)thiazolo[5,4-b]pyridin-2-amine hydrochloride

HRID 335128Notes

Reaction equation

HRID 335128 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:5]([NH2:8])=[N:6][CH:7]=1.[Cl:16][C:17]1[C:22]([N:23]=[C:24]=[S:25])=[CH:21][CH:20]=[CH:19][N:18]=1.CN(C=O)C>C(Cl)Cl>[ClH:16].[Br:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:5]([NH:8][C:24]2[S:25][C:17]3[C:22]([N:23]=2)=[CH:21][CH:20]=[CH:19][N:18]=3)=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 128680882-Chloro-3-isothiocyanatopyridineHCID 459260645-Bromo-3-(phenylthio)pyridin-2-amine

Product 1

HCID 86678229N-(5-bromo-3-(phenylthio)pyridin-2-yl)thiazolo[5,4-b]pyridin-2-amine hydrochlorideYield 61%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

mL 5-Bromo-3-(phenylthio)pyridin-2-amine (1.0 g, 3.6 mmol), 2-chloro-3-isothiocyanatopyridine (0.61 g, 3.6 mmol), DMF (2 mL) were heated to 90° C. for 8 hours. Cooled to ambient temperature and the solids were diluted with mL CH2Cl2 (2 mL) and filtered and washed with small amount of CH2Cl2 to afford the title compound (0.98 g, 61% yield). 1H NMR (d6-DMSO) δ 8.50 (d, 1H), 8.39 (dd, 1H), 7.98 (s, 1H), 7.92 (dd, 1 h), 7.38-7.25 (m, 6H). Mass spectrum (apci) m/z=414.8 (M+H).

Workup

  1. filtrationfiltered
  2. washwashed with small amount of CH2Cl2

Sources & evidence

ORD record
ord-2fb1d5029464444ab4690c63a33acf6b
Source dataset
uspto-grants-2014_11
Patent number
US08883828B2

Reaction notes

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