Hydrochloric Acid → 1-(4-(2-(3-Phenoxy-5-(pyridin-2-ylthio)pyridin-2-ylamino)thiazol-4-yl)piperidin-1-yl)ethanone dihydrochloride

HRID 1809581Notes

Reaction equation

HRID 1809581 reaction equation
[O:1]([C:8]1[C:9]([NH:21][C:22]([NH2:24])=[S:23])=[N:10][CH:11]=[C:12]([S:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)[CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:32]([N:35]1[CH2:40][CH2:39][CH:38]([C:41](=O)[CH2:42]Br)[CH2:37][CH2:36]1)(=[O:34])[CH3:33].[ClH:45]>C(O)C>[ClH:45].[ClH:45].[O:1]([C:8]1[C:9]([NH:21][C:22]2[S:23][CH:42]=[C:41]([CH:38]3[CH2:39][CH2:40][N:35]([C:32](=[O:34])[CH3:33])[CH2:36][CH2:37]3)[N:24]=2)=[N:10][CH:11]=[C:12]([S:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)[CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 772303261-(1-Acetylpiperidin-4-yl)-2-bromoethan-1-oneHCID 866410901-(3-Phenoxy-5-(pyridin-2-ylthio)pyridin-2-yl)thiourea

Product 1

HCID 866410911-(4-(2-(3-Phenoxy-5-(pyridin-2-ylthio)pyridin-2-ylamino)thiazol-4-yl)piperidin-1-yl)ethanone dihydrochlorideYield 76.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-(3-phenoxy-5-(pyridin-2-ylthio)pyridin-2-yl)thiourea (0.075 g, 0.21 mmol), triethylamine (0.073 mL, 0.53 mmol), and 1-(1-acetylpiperidin-4-yl)-2-bromoethanone (0.087 g, 0.26 mmol) was refluxed in Ethanol (10 mL) for 3 hours. The reaction was concentrated and the residue was purified by silica gel (1% MeOH in CH2Cl2) to provide 1-(4-(2-(3-phenoxy-5-(pyridin-2-ylthio)pyridin-2-ylamino)thiazol-4-yl)piperidin-1-yl)ethanone dihydrochloride (0.093 g, 76.2% yield) after HCl salt formation. 1H NMR (d6-DMSO) δ 8.38 (m, 1H), 8.29 (d, 1H), 7.67 (dt, 1H), 7.45-7.37 (m, 3H), 7.21-7.08 (m, 5H), 6.78 (s, 1H), 4.32 (d, 1H), 3.87 (d, 1H), 3.13 (t, 1H), 2.87 (m, 1H), 2.64 (t, 1H), 2.01 (s, 3H), 1.95 (m, 2H), 1.63-1.39 (m, 2H).

Workup

  1. concentrationThe reaction was concentrated
  2. customthe residue was purified by silica gel (1% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-7746819c8f0742ada1aac04202ca7adf
Source dataset
uspto-grants-2013_01
Patent number
US08362037B2

Reaction notes

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