Trifluoroacetic acid → 2-((1-(5-Chloropyrimidin-2-yl)piperidin-4-yl)oxy)-6-(piperidin-4-yl)benzo[d]thiazole

HRID 1429581Notes

Reaction equation

HRID 1429581 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([O:14][C:15]3[S:16][C:17]4[CH:23]=[C:22]([CH:24]5[CH2:29][CH2:28][N:27](C(OC(C)(C)C)=O)[CH2:26][CH2:25]5)[CH:21]=[CH:20][C:18]=4[N:19]=3)[CH2:10][CH2:9]2)=[N:6][CH:7]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[N:6][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([O:14][C:15]3[S:16][C:17]4[CH:23]=[C:22]([CH:24]5[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]5)[CH:21]=[CH:20][C:18]=4[N:19]=3)[CH2:10][CH2:9]2)=[N:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67467599Tert-butyl 4-(2-((1-(5-chloropyrimidin-2-yl)piperidin-4-yl)oxy)benzo[d]thiazol-6-yl)piperidine-1-carboxylate

Product 1

HCID 674682802-((1-(5-Chloropyrimidin-2-yl)piperidin-4-yl)oxy)-6-(piperidin-4-yl)benzo[d]thiazoleYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of tert-butyl 4-(2-((1-(5-chloropyrimidin-2-yl)piperidin-4-yl)oxy)benzo[d]thiazol-6-yl)piperidine-1-carboxylate (133 mg, 0.251 mmol) in CH2Cl2 (2.5 mL) was added TFA (0.2 mL, 2.5 mmol). The reaction mixture was stirred at rt for 3 h. The reaction mixture was diluted with CH2Cl2 (5 mL) and washed with aq. NaOH (1 N, 3 mL) and brine. The organic layer was dried (Na2SO4), filtered, and concentrated to afford 2-((1-(5-chloropyrimidin-2-yl)piperidin-4-yl)oxy)-6-(piperidin-4-yl)benzo[d]thiazole (102 mg, 0.237 mmol, 95% yield) as a pale yellow solid. LCMS (m/z)=430 (M+H)+.

Workup

  1. washwashed with aq. NaOH (1 N, 3 mL) and brine
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-0027a0a816dc4cc2ae817ad5ebd78219
Source dataset
uspto-grants-2015_01
Patent number
US08940716B2

Reaction notes

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