Trifluoroacetic acid → 2-(1-(5-Methyl-1,3,4-thiadiazol-2-yl)piperidin-4-yloxy)-6-(1,2,3,6-tetrahydropyridin-4-yl)benzo[d]thiazole

HRID 1429558Notes

Reaction equation

HRID 1429558 reaction equation
[CH3:1][C:2]1[S:6][C:5]([N:7]2[CH2:12][CH2:11][CH:10]([O:13][C:14]3[S:15][C:16]4[CH:22]=[C:21]([C:23]5[CH2:28][CH2:27][N:26](C(OC(C)(C)C)=O)[CH2:25][CH:24]=5)[CH:20]=[CH:19][C:17]=4[N:18]=3)[CH2:9][CH2:8]2)=[N:4][N:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][C:2]1[S:6][C:5]([N:7]2[CH2:12][CH2:11][CH:10]([O:13][C:14]3[S:15][C:16]4[CH:22]=[C:21]([C:23]5[CH2:28][CH2:27][NH:26][CH2:25][CH:24]=5)[CH:20]=[CH:19][C:17]=4[N:18]=3)[CH2:9][CH2:8]2)=[N:4][N:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67468486tert-butyl 4-(2-(1-(5-methyl-1,3,4-thiadiazol-2-yl)piperidin-4-yloxy)benzo[d]thiazol-6-yl)-5,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 674670502-(1-(5-Methyl-1,3,4-thiadiazol-2-yl)piperidin-4-yloxy)-6-(1,2,3,6-tetrahydropyridin-4-yl)benzo[d]thiazoleYield 100.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of tert-butyl 4-(2-(1-(5-methyl-1,3,4-thiadiazol-2-yl)piperidin-4-yloxy)benzo[d]thiazol-6-yl)-5,6-dihydropyridine-1(2H)-carboxylate (443 mg, 0.862 mmol) in CH2Cl2 (7 mL) at rt was added TFA (1.0 mL, 13 mmol). The reaction mixture was stirred at rt overnight. The mixture was diluted with CH2Cl2 (10 mL), washed with aq. NaOH (1 N, 15 mL), then brine. The organic layer was dried (Na2SO4), filtered, and concentrated to afford 2-(1-(5-methyl-1,3,4-thiadiazol-2-yl)piperidin-4-yloxy)-6-(1,2,3,6-tetrahydropyridin-4-yl)benzo[d]thiazole (357 mg, 0.863 mmol, 100% yield) as a yellow solid. LCMS (m/z)=414 (M+H)+.

Workup

  1. washwashed with aq. NaOH (1 N, 15 mL)
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b48221ac64b74735bc14c704d23f4c23
Source dataset
uspto-grants-2015_01
Patent number
US08940716B2

Reaction notes

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