Ammonium Chloride → N-(2-Chloro-[3,4']bipyridinyl-3'-yl)-3-methanesulfonyl-N-methyl-5-trifluoromethyl-benzamide

HRID 878378Notes

Reaction equation

HRID 878378 reaction equation
ClC1C(C2C=CN=CC=2NC)=CC=CN=1.F[C:17]1[CH:22]=[CH:21]C=[C:19](OC)[C:18]=1[C:25]1[CH:30]=[CH:29][N:28]=[CH:27][C:26]=1[N:31]([CH2:48]C(F)(F)F)[C:32](=[O:47])[C:33]1[CH:38]=[C:37]([C:39]([F:42])([F:41])[F:40])[CH:36]=[C:35]([S:43]([CH3:46])(=[O:45])=[O:44])[CH:34]=1.CCN(C(C)C)C(C)C.[NH4+:62].[Cl-:63]>C(Cl)Cl>[Cl:63][C:19]1[C:18]([C:25]2[CH:30]=[CH:29][N:28]=[CH:27][C:26]=2[N:31]([CH3:48])[C:32](=[O:47])[C:33]2[CH:38]=[C:37]([C:39]([F:42])([F:41])[F:40])[CH:36]=[C:35]([S:43]([CH3:46])(=[O:44])=[O:45])[CH:34]=2)=[CH:17][CH:22]=[CH:21][N:62]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 86670807N-[4-(2-Fluoro-6-methoxy-phenyl)-pyridin-3-yl]-3-methanesulfonyl-N-(2,2,2-trifluoro-ethyl)-5-trifluoromethyl-benzamide2×HCID 866708262-chloro-N-methyl-3,4'-bipyridin-3'-amine

Product 1

HCID 86670825N-(2-Chloro-[3,4']bipyridinyl-3'-yl)-3-methanesulfonyl-N-methyl-5-trifluoromethyl-benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-chloro-N-methyl-3,4′-bipyridin-3′-amine (0.2 g, 910 μmol, example 313, intermediate a) in CH2Cl2 (5 mL) were added 3-(methylsulfonyl)-5-(trifluoromethyl)benzoyl chloride (522 mg, 1.82 mmol, example 223, intermediate d) and DIPEA (471 mg, 636 μL, 3.64 mmol) and the light yellow solution was stirred at room temperature for 16 hours. The reaction mixture was poured on saturated aqueous NH4Cl solution and CH2Cl2 and the layers were separated. The aqueous layer was extracted four times with CH2Cl2. The organic layers dried over MgSO4, filtered, treated with silica gel and evaporated. The compound was purified by silica gel chromatography on a 10 g column using a MPLC system eluting with a gradient of n-heptane:EtOAc (100:0 to 0:100). Light brown foam (0.393 g; 91%). MS (ESI): m/z=470.06 [M+H]+.

Workup

  1. customthe layers were separated
  2. extractionThe aqueous layer was extracted four times with CH2Cl2
  3. dry with materialThe organic layers dried over MgSO4
  4. filtrationfiltered
  5. additiontreated with silica gel
  6. customevaporated
  7. customThe compound was purified by silica gel chromatography on a 10 g column
  8. washeluting with a gradient of n-heptane:EtOAc (100:0 to 0:100)

Sources & evidence

ORD record
ord-fb35a5159b8146c8ba4a4a5f3c2aaa82
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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