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

HRID 2080192Notes

Reaction equation

HRID 2080192 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].C1C=CC(CC(NCN[C@H](C(O)=O)CC2C=CC([N+]([O-])=O)=CC=2)=O)=CC=1.[N:51]1[CH:56]=[CH:55][CH:54]=[CH:53][C:52]=1[CH2:57][CH2:58][NH2:59].O>CS(C)=O.C(N(CC)C(C)C)(C)C.C(OCC)(=O)C>[NH2:1][C:2]1[N:23]=[C:22]([NH:59][CH2:58][CH2:57][C:52]2[CH:53]=[CH:54][CH:55]=[CH:56][N:51]=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

8

Reactant 4

HCID 962WaterHCID 759192-PyridineethanamineHCID 188218A-101HCID 231304982-aminochloro-N-(5-phenoxy-thiophen-2-ylmethyl)-nicotinamide

Product 1

HCID 231307702-Amino-N-(5-phenoxy-thiophen-2-ylmethyl)-6-(2-pyridin-2-yl-ethylamino)-nicotinamide

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolventHCID 81531DiisopropylethylamineSolvent

Conditions

Temperature
130 °C

Procedure

2-Amino-6-chloro-N-(5-phenoxy-thiophen-2-ylmethyl)-nicotinamide described in Example A-101 (20 mg, 37 μmol) and 2-pyridin-2-yl-ethyl amine (66 μl, 0.56 mmol) were dissolved in a mixture solvent of dimethylsulfoxide (1 mL) and N,N-diisopropylethylamine (0.5 mL), and the solution was stirred at 130° C. for 17 hours. The reaction solution was cooled to room temperature, water and ethyl acetate were added, the organic layer was partitioned, washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated in vacuo, the residue was purified by reverse phase high performance liquid chromatography (acetonitrile-water mobile phase (containing 0.1% trifluoroacetic acid) was used), and the title compound (17.7 mg) was obtained as a trifluoroacetic acid salt.

Workup

  1. temperatureThe reaction solution was cooled to room temperature
  2. customthe organic layer was partitioned
  3. washwashed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated in vacuo
  6. customthe residue was purified by reverse phase high performance liquid chromatography (acetonitrile-water mobile phase (containing 0.1% trifluoroacetic acid) was used)

Sources & evidence

ORD record
ord-81b4d7f412fd461a9709844e487b421d
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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