Ammonium Chloride → HCID 86670822, compound

HRID 878363Notes

Reaction equation

HRID 878363 reaction equation
[F:1][C:2]([F:21])([F:20])[O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[CH:15]=[CH:14][N:13]=[CH:12][C:11]=1[NH:16][CH2:17][C:18]#[N:19].FC1C=CC=C(OC)C=1C1C=CN=CC=1N(CC(F)(F)F)[C:38](=[O:53])[C:39]1[CH:44]=[C:43]([C:45]([F:48])([F:47])[F:46])[CH:42]=[C:41]([S:49]([CH3:52])(=[O:51])=[O:50])[CH:40]=1.CCN(C(C)C)C(C)C.[NH4+].[Cl-]>C(Cl)Cl>[C:18]([CH2:17][N:16]([C:11]1[CH:12]=[N:13][CH:14]=[CH:15][C:10]=1[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[O:3][C:2]([F:1])([F:20])[F:21])[C:38](=[O:53])[C:39]1[CH:44]=[C:43]([C:45]([F:48])([F:46])[F:47])[CH:42]=[C:41]([S:49]([CH3:52])(=[O:51])=[O:50])[CH:40]=1)#[N:19]

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 86670823HCID 86670823, compound

Product 1

HCID 86670822HCID 86670822, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-(4-(2-(trifluoromethoxy)phenyl)pyridin-3-ylamino)acetonitrile (0.07 g, 239 μmol) in CH2Cl2 (2 mL) were added 3-(methylsulfonyl)-5-(trifluoromethyl)benzoyl chloride (137 mg, 477 μmol, example 223, intermediate d) and DIPEA (123 mg, 167 μL, 955 μmol) and the clear, yellow solution was stirred at room temperature for 18 hours. The reaction mixture was poured on saturated aqueous NH4Cl solution and CH2Cl2 and the layers were separated. The aqueous layer was extracted three times with CH2Cl2. The organic layers were dried over MgSO4, filtered, treated with silica gel and evaporated. The compound was purified by silica gel chromatography on a 20 g column using a MPLC system eluting with a gradient of n-heptane:EtOAc (100:0 to 0:100). The product was purified by preparative HPLC (Gemini NX column) using a gradient of MeOH:water (containing 0.1% formic acid) (20:80 to 98:2). Colorless solid (0.085 g; 65%). MS (ESI): m/z=544.08 [M+H]+.

Workup

  1. customthe layers were separated
  2. extractionThe aqueous layer was extracted three times with CH2Cl2
  3. dry with materialThe organic layers were dried over MgSO4
  4. filtrationfiltered
  5. additiontreated with silica gel
  6. customevaporated
  7. customThe compound was purified by silica gel chromatography on a 20 g column
  8. washeluting with a gradient of n-heptane:EtOAc (100:0 to 0:100)
  9. customThe product was purified by preparative HPLC (Gemini NX column)

Sources & evidence

ORD record
ord-f9da6c8455e9429392e974d9997dd1cf
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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