Water → 2-Amino-6-(2-(4-nitro-phenylamino)-ethylamino)-N-(5-phenoxy-thiophen-2-ylmethyl)-nicotinamide

HRID 2079972Notes

Reaction equation

HRID 2079972 reaction equation
[NH2:1][C:2]1[N:23]=[C:22]([NH:24][CH2:25][CH2:26][NH2:27])[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].F[C:29]1[CH:34]=[CH:33][C:32]([N+:35]([O-:37])=[O:36])=[CH:31][CH:30]=1.C(N(CC)C(C)C)(C)C.O>CS(C)=O>[NH2:1][C:2]1[N:23]=[C:22]([NH:24][CH2:25][CH2:26][NH:27][C:29]2[CH:34]=[CH:33][C:32]([N+:35]([O-:37])=[O:36])=[CH:31][CH:30]=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

6

Reactant 4

HCID 962WaterHCID 9590p-FluoronitrobenzeneHCID 81531DiisopropylethylamineHCID 231305652-Amino-6-(2-amino-ethylamino)-N-(5-phenoxy-thiophen-2-ylmethyl)-nicotinamide

Product 1

HCID 231307092-Amino-6-(2-(4-nitro-phenylamino)-ethylamino)-N-(5-phenoxy-thiophen-2-ylmethyl)-nicotinamideYield 70.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

2-Amino-6-(2-amino-ethylamino)-N-(5-phenoxy-thiophen-2-ylmethyl)-nicotinamide (25 mg, 65 μmol) described in Preparation Example A+-12, 4-fluoronitrobenzene (7.6 μl, 71 μmol) and N,N-diisopropylethylamine (22.7 μl, 130 μmol) were dissolved in dimethylsulfoxide (0.5 mL), the solution was stirred for 3.5 hours at room temperature, and then, the solution was stirred for 15.5 hours at 70° C. The reaction solution was cooled to room temperature, water was added, the solution was extracted with ethyl acetate, the organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was evaporated in vacuo, residue was purified by reverse phase high performance liquid chromatography (mobile phase:acetonitrile-water (containing 0.1% trifluoroacetic acid) was used), and the title compound (23 mg) was obtained as a trifluoroacetic acid salt.

Workup

  1. stirringthe solution was stirred for 15.5 hours at 70° C
  2. temperatureThe reaction solution was cooled to room temperature
  3. extractionthe solution was extracted with ethyl acetate
  4. washthe organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated in vacuo, residue
  7. customwas purified by reverse phase high performance liquid chromatography (mobile phase:acetonitrile-water (containing 0.1% trifluoroacetic acid) was used)

Sources & evidence

ORD record
ord-a04f615fd39446b7973e4066f8f54595
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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