Ammonium Chloride → HCID 70663482, compound

HRID 878260Notes

Reaction equation

HRID 878260 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][C:9]=2[N:14]([CH3:28])[C:15](=[O:27])[C:16]2[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[C:18]([SH:26])[CH:17]=2)=[C:4]([O:29][CH3:30])[CH:3]=1.CCN(C(C)C)C(C)C.Br[CH2:41][CH2:42][C:43]([O:45][CH3:46])=[O:44].[NH4+].[Cl-]>C(#N)C.CCOC(C)=O>[CH3:46][O:45][C:43](=[O:44])[CH2:42][CH2:41][S:26][C:18]1[CH:19]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:21]=[C:16]([C:15](=[O:27])[N:14]([C:9]2[CH:10]=[N:11][CH:12]=[CH:13][C:8]=2[C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][C:4]=2[O:29][CH3:30])[CH3:28])[CH:17]=1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 76934Methyl 3-bromopropanoateHCID 81531DiisopropylethylamineHCID 70663556HCID 70663556, compound

Product 1

HCID 70663482HCID 70663482, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of N-(4-(4-fluoro-2-methoxyphenyl)pyridin-3-yl)-3-mercapto-N-methyl-5-(trifluoromethyl)benzamide (0.2 g, 458 μmol, example 216, intermediate a) in acetonitrile (4 mL) were added DIPEA (118 mg, 160 μL, 917 μmol) and methyl 3-bromopropanoate (91.8 mg, 60.0 μL, 550 μmol) and the clear and colorless solution was stirred at room temperature for 2.25 hours. The reaction mixture was poured on saturated aqueous NH4Cl solution and EtOAc and the layers were separated. The aqueous layer was extracted twice with EtOAc. The organic layers were filtered, treated with silica gel and evaporated. The compound was purified by silica gel chromatography on a 10 g column using an MPLC system eluting with a gradient of n-heptane:EtOAc (100:0 to 0:100). Colorless solid (0.178 g; 74%). MS (ESI): m/z=523.13 [M+H]+.

Workup

  1. customthe layers were separated
  2. extractionThe aqueous layer was extracted twice with EtOAc
  3. filtrationThe organic layers were filtered
  4. additiontreated with silica gel
  5. customevaporated
  6. customThe compound was purified by silica gel chromatography on a 10 g column
  7. washeluting with a gradient of n-heptane:EtOAc (100:0 to 0:100)

Sources & evidence

ORD record
ord-94e51ebd7d754ddb8072aff4a7a9f414
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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