N-(4-methoxybenzyl)-3-(5-(2,3-dichlorophenyl)thiazol-4-yl)-5-(pyridin-3-yl)pyridin-2-amine → 3-(5-(2,3-Dichlorophenyl)thiazol-4-yl)-5-(pyridin-3-yl)pyridin-2-amine

HRID 253980Notes

Reaction equation

HRID 253980 reaction equation
COC1C=CC(C[NH:8][C:9]2[C:14]([C:15]3[N:16]=[CH:17][S:18][C:19]=3[C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[C:21]=3[Cl:27])=[CH:13][C:12]([C:28]3[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=3)=[CH:11][N:10]=2)=CC=1>C(O)(C(F)(F)F)=O>[Cl:27][C:21]1[C:22]([Cl:26])=[CH:23][CH:24]=[CH:25][C:20]=1[C:19]1[S:18][CH:17]=[N:16][C:15]=1[C:14]1[C:9]([NH2:8])=[N:10][CH:11]=[C:12]([C:28]2[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=2)[CH:13]=1

Participants

3

Reactant 1

HCID 58179588N-(4-methoxybenzyl)-3-(5-(2,3-dichlorophenyl)thiazol-4-yl)-5-(pyridin-3-yl)pyridin-2-amine

Product 1

HCID 581796123-(5-(2,3-Dichlorophenyl)thiazol-4-yl)-5-(pyridin-3-yl)pyridin-2-amineYield 9%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of N-(4-methoxybenzyl)-3-(5-(2,3-dichlorophenyl)thiazol-4-yl)-5-(pyridin-3-yl)pyridin-2-amine (24 mg, 0.046 mmol) in TFA (1 mL) was heated to reflux overnight. The solvent was removed in vacuo and the compound was purified by reversed-phase HPLC to provide 3-(5-(2,3-dichlorophenyl)thiazol-4-yl)-5-(pyridin-3-yl)pyridin-2-amine as a while solid [2.2 mg, 9% yield; LC-MS M+H=399.2; 1H-NMR (300 MHz, methanol-d4) 9.34 (1H, s), 8.57 (1H, dd), 8.41 (1H, d), 8.28 (1H, d), 7.79 (1H, d), 7.71 (1H, dd), 7.58 (1H, dd), 7.57 (1H, t), 7.46 (1H, t), 2.64 (3H, s)].

Workup

  1. temperatureto reflux overnight
  2. customThe solvent was removed in vacuo
  3. customthe compound was purified by reversed-phase HPLC

Sources & evidence

ORD record
ord-0081ed3d72304d88beddf9b5b202869b
Source dataset
uspto-grants-2011_01
Patent number
US07872031B2

Reaction notes

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