Acetic Acid → HCID 86681219, compound

HRID 1848246Notes

Reaction equation

HRID 1848246 reaction equation
[CH3:1][S:2][C:3]1[S:4][C:5]2[CH:11]=[C:10]([CH2:12][NH:13][C:14]3[C:19]([N+:20]([O-])=O)=[CH:18][C:17]([C:23]([F:26])([F:25])[F:24])=[CH:16][N:15]=3)[CH:9]=[CH:8][C:6]=2[N:7]=1.CC(O)=O.CO>C(Cl)Cl.[Zn]>[CH3:1][S:2][C:3]1[S:4][C:5]2[CH:11]=[C:10]([CH2:12][NH:13][C:14]3[C:19]([NH2:20])=[CH:18][C:17]([C:23]([F:26])([F:24])[F:25])=[CH:16][N:15]=3)[CH:9]=[CH:8][C:6]=2[N:7]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 887MethanolHCID 86681218HCID 86681218, compound

Product 1

HCID 86681219HCID 86681219, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of N-((2-(methylthio)benzo[d]thiazol-6-yl)methyl)-3-nitro-5-(trifluoromethyl)pyridin-2-amine (0.97 g, 2.42 mmol), HOAc (4 mL), and MeOH (4 mL) in DCM (30 mL) cooled in ice-water bath was slowly added zinc dust (1.6 g, 24.2 mmol). The reaction mixture was stirred at 0° C. for 2 h. The mixture was filtered and the filtrate was diluted with DCM and then washed with water and aq NaHCO3. The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure to afford N2-((2-(methylthio)benzo[d]thiazol-6-yl)methyl)-5-(trifluoromethyl)pyridine-2,3-diamine (0.89 g, 100%). 1H NMR (300 MHz, DMSO-d6) δ 8.05 (s, 1H), 7.82 (d, J=8.4 Hz, 1H), 7.77 (s, 1H), 7.44-7.41 (m, 1H), 7.03 (d, J=1.8 Hz, 1H), 4.84 (br s, 1H), 4.78 (d, J=5.1 Hz, 2H), 3.29 (br s, 2H), 2.79 (s, 3H). LCMS (ESI) m/z 371 (M+H)+.

Workup

  1. filtrationThe mixture was filtered
  2. additionthe filtrate was diluted with DCM
  3. washwashed with water and aq NaHCO3
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6ea7e110080e4fbeb429c5ad99b17fb1
Source dataset
uspto-grants-2015_02
Patent number
US08952058B2

Reaction notes

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