Water → 2-Amino-6-(2-amino-ethylamino)-N-(5-phenoxy-thiophen-2-ylmethyl)-nicotinamide

HRID 2079971Notes

Reaction equation

HRID 2079971 reaction equation
[NH2:1][C:2]1[N:23]=[C:22](Cl)[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].[CH2:25]([NH2:28])[CH2:26][NH2:27].O>CS(C)=O.C(N(CC)C(C)C)(C)C>[NH2:1][C:2]1[N:23]=[C:22]([NH:27][CH2:26][CH2:25][NH2:28])[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 3

HCID 962WaterHCID 3301EthylenediamineHCID 231304982-aminochloro-N-(5-phenoxy-thiophen-2-ylmethyl)-nicotinamide

Product 1

HCID 231305652-Amino-6-(2-amino-ethylamino)-N-(5-phenoxy-thiophen-2-ylmethyl)-nicotinamideYield 60%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 81531DiisopropylethylamineSolvent

Conditions

Temperature
120 °C

Procedure

2-Amino-6-chloro-N-(5-phenoxy-thiophen-2-ylmethyl)-nicotinamide (150 mg, 0.417 mmol) described in Preparation Example A+-11, ethane-1,2-diamine (418 μl, 6.25 mmol) were dissolved in a mixture solution of dimethylsulfoxide (2 mL) and N,N-diisopropylethylamine (1 mL), and the solution was stirred at 120° C. for 15 hours. The reaction solution was cooled to room temperature, water was added, then extracted with ethyl acetate and tetrahydrofuran, the organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was evaporated in vacuo, tetrahydrofuran and NH silica gel were added to the residue, the solvent was evaporated in vacuo adsorption, purification was carried out by NH silica gel column chromatography (ethyl acetate:methanol=10:1), and the title compound (95 mg, 0.25 mmol, 59%) was obtained as a white solid.

Workup

  1. temperatureThe reaction solution was cooled to room temperature
  2. extractionextracted with ethyl acetate and tetrahydrofuran
  3. washthe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated in vacuo, tetrahydrofuran and NH silica gel
  6. additionwere added to the residue
  7. customthe solvent was evaporated in vacuo adsorption, purification

Sources & evidence

ORD record
ord-b1570c3853654678a6e59cfb477bbc07
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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