Ammonia → HCID 23130733, compound

HRID 2080201Notes

Reaction equation

HRID 2080201 reaction equation
[NH2:1][C:2]1[N:23]=[C:22]([CH:24]=[CH2:25])[CH:21]=[CH:20][C:3]=1[C:4]([NH:6][CH2:7][C:8]1[S:9][C:10]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:11][CH:12]=1)=[O:5].C.[I].[I].[CH2:29]([Zn]CC)C.N>C(#N)C.O.FC(F)(F)C(O)=O.C(OCC)(=O)C.O.C1(C)C=CC=CC=1>[NH2:1][C:2]1[N:23]=[C:22]([CH:24]2[CH2:29][CH2:25]2)[CH:21]=[CH:20][C:3]=1[C:4]([NH:6][CH2:7][C:8]1[S:9][C:10]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:11][CH:12]=1)=[O:5]

Participants

10

Reactant 4

HCID 222AmmoniaHCID 23130722HCID 23130722, compoundHCID 178418750HCID 178418750, compoundHCID 178477805HCID 178477805, compound

Product 1

HCID 23130733HCID 23130733, compoundYield 4.9%

Reagents, catalysts & solvents 5

HCID 962WaterSolventHCID 1140TolueneSolventHCID 6422Trifluoroacetic acidSolvent2×HCID 8857Ethyl AcetateSolventHCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

To a mixture of 2-amino-N-(5-phenoxy-thiophen-2-ylmethyl)-6-vinyl-nicotinamide described in Example A-168 (6.0 mg, 0.017 mmol) and toluene (0.5 mL) were added diiodine methane (0.0055 mL, 0.068 mmol) and diethyl zinc (1.1M toluene solution, 0.046 mL, 0.051 mmol) on an ice bath, and the solution was stirred at room temperature for 30 minutes. Water, ethyl acetate and an aqueous solution of 29% ammonia were added to the reaction solution for extraction, the organic layer was then washed with brine. The organic layer was evaporated in vacuo, then, residue was purified by reverse phase high performance liquid chromatography (acetonitrile-water mobile phase (containing 0.1% trifluoroacetic acid) was used), and trifluoroacetic acid salt of the title compound (0.40 mg, 0.00083 mmol, 4.9%) was obtained.

Workup

  1. washthe organic layer was then washed with brine
  2. customThe organic layer was evaporated in vacuo

Sources & evidence

ORD record
ord-eb4b89bf2f254350bc279d75e68f0b60
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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