1,4-Dioxane → (S)-6-(2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yloxy)-N-(piperidin-3-yl)benzo[d]thiazol-2-amine

HRID 1922243

Reaction equation

HRID 1922243 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[C:11]([O:13][C:14]3[CH:36]=[CH:35][C:17]4[N:18]=[C:19]([NH:21][C@H:22]5[CH2:27][CH2:26][CH2:25][N:24](C(OC(C)(C)C)=O)[CH2:23]5)[S:20][C:16]=4[CH:15]=3)[CH:10]=[CH:9][N:8]=2)[CH:4]=[N:3]1.O1CCOCC1>Cl>[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[C:11]([O:13][C:14]3[CH:36]=[CH:35][C:17]4[N:18]=[C:19]([NH:21][C@H:22]5[CH2:27][CH2:26][CH2:25][NH:24][CH2:23]5)[S:20][C:16]=4[CH:15]=3)[CH:10]=[CH:9][N:8]=2)[CH:4]=[N:3]1

Participants

4

Reactant 2

HCID 312751,4-DioxaneHCID 57725561(S)-tert-butyl 3-(6-(2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yloxy)benzo[d]thiazol-2-ylamino)piperidine-1-carboxylate

Product 1

HCID 57725571(S)-6-(2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yloxy)-N-(piperidin-3-yl)benzo[d]thiazol-2-amineYield 94.7%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

(S)-tert-butyl 3-(6-(2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yloxy)benzo[d]thiazol-2-ylamino)piperidine-1-carboxylate (9.6 mg, 19 μmol) was dissolved in 1 ml of 4M HCl in dioxane (4 mmol). The reaction solution was stirred at room temperature for 1 hour. The crude reaction solution was evaporated in vacuo to give (S)-6-(2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yloxy)-N-(piperidin-3-yl)benzo[d]thiazol-2-amine (7.6 mg, 18 μmol) as white solid. ES/MS m/z 407.1 (MH+).

Workup

  1. customThe crude reaction solution
  2. customwas evaporated in vacuo

Sources & evidence

ORD record
ord-892162a79d814bd982e9b00c2a23f75f
Source dataset
uspto-grants-2012_05
Patent number
US08173689B2

Linked notes

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