Triethylamine → HCID 86681218, compound

HRID 1848245Notes

Reaction equation

HRID 1848245 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([C:11]([F:14])([F:13])[F:12])=[CH:4][N:3]=1.[CH3:15][S:16][C:17]1[S:18][C:19]2[CH:25]=[C:24]([CH2:26][NH2:27])[CH:23]=[CH:22][C:20]=2[N:21]=1.C(N(CC)CC)C>CN(C=O)C.CCOC(C)=O>[CH3:15][S:16][C:17]1[S:18][C:19]2[CH:25]=[C:24]([CH2:26][NH:27][C:2]3[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([C:11]([F:14])([F:13])[F:12])=[CH:4][N:3]=3)[CH:23]=[CH:22][C:20]=2[N:21]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 47369502-Chloro-3-nitro-5-(trifluoromethyl)pyridineHCID 86681009HCID 86681009, compound

Product 1

HCID 86681218HCID 86681218, compoundYield 84.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-chloro-3-nitro-5-(trifluoromethyl)pyridine (500 mg, 2.21 mmol), (2-(methylthio)benzo[d]thiazol-6-yl)methanamine from Step 4 of Example 23 (583 mg, 2.76 mmol), and triethylamine (837 mg, 8.29 mmol) in DMF (10 mL) was stirred at rt overnight. The reaction mixture was diluted with EtOAc and washed with water. The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography eluting with 1:0 to 10:1 petroleum ether/EtOAc to give N-((2-(methylthio)benzo[d]thiazol-6-yl)methyl)-3-nitro-5-(trifluoromethyl)pyridin-2-amine as a yellow solid (150 mg, 84.7%). 1H NMR (300 MHz, DMSO-d6) δ 9.46 (t, J=1.8 Hz, 1H), 8.78 (d, J=2.1 Hz, 1H), 8.66 (d, J=2.4 Hz, 1H), 7.97 (s, 1H), 7.78 (d, J=8.4 Hz, 1H), 7.49-7.45 (m, 1H), 4.95 (d, J=6.6 Hz, 2H), 2.77 (s, 3H); LCMS (ESI) m/z 401 (M+H)+.

Workup

  1. washwashed with water
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel chromatography
  6. washeluting with 1:0 to 10:1 petroleum ether/EtOAc

Sources & evidence

ORD record
ord-220ec2e095984596ab0cd11082fabe37
Source dataset
uspto-grants-2015_02
Patent number
US08952058B2

Reaction notes

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