Hydrochloric Acid → N-(piperidin-4-yl)-6-(1-(4-(trifluoromethyl)phenyl)piperidin-4-yloxy)benzo[d]thiazole-2-carboxamide

HRID 539824Notes

Reaction equation

HRID 539824 reaction equation
[F:1][C:2]([F:42])([F:41])[C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][CH:12]([O:15][C:16]3[CH:40]=[CH:39][C:19]4[N:20]=[C:21]([C:23]([NH:25][CH:26]5[CH2:31][CH2:30][N:29](C(OC(C)(C)C)=O)[CH2:28][CH2:27]5)=[O:24])[S:22][C:18]=4[CH:17]=3)[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.Cl>O1CCOCC1>[NH:29]1[CH2:30][CH2:31][CH:26]([NH:25][C:23]([C:21]2[S:22][C:18]3[CH:17]=[C:16]([O:15][CH:12]4[CH2:11][CH2:10][N:9]([C:6]5[CH:5]=[CH:4][C:3]([C:2]([F:42])([F:1])[F:41])=[CH:8][CH:7]=5)[CH2:14][CH2:13]4)[CH:40]=[CH:39][C:19]=3[N:20]=2)=[O:24])[CH2:27][CH2:28]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57951083Tert-butyl 4-(6-(1-(4-(trifluoromethyl)phenyl)piperidin-4-yloxy)benzo[d]thiazole-2-carboxamido)piperidine-1-carboxylate2×

Product 1

HCID 57951054N-(piperidin-4-yl)-6-(1-(4-(trifluoromethyl)phenyl)piperidin-4-yloxy)benzo[d]thiazole-2-carboxamideYield 110.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of tert-butyl 4-(6-(1-(4-(trifluoromethyl)phenyl)piperidin-4-yloxy)benzo[d]thiazole-2-carboxamido)piperidine-1-carboxylate (compound 8) (0.16 g, 0.27 mmol) and 4N hydrochloric acid in dioxane (2 mL) was stirred at room temperature for 1 h. The reaction mixture was concentrated and washed with diethyl ether (2×3 mL) and then dried under reduced pressure to afford N-(piperidin-4-yl)-6-(1-(4-(trifluoromethyl)phenyl)piperidin-4-yloxy)benzo[d]thiazole-2-carboxamide as a off-white solid (0.15 g, 99%). 1H NMR (CD3OD, 300 MHz) 7.83 (m, 5H), 7.48 (s, 1H), 7.23 (m, 1H), 4.93 (m, 1H), 4.22 (m, 1H), 3.90 (m, 3H), 3.35 (m, 2H), 3.17 (m, 2H), 2.23 (m, 8H), 1.98 (m, 2H) ppm; MS (ES) 489.1 (M+1).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. washwashed with diethyl ether (2×3 mL)
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-4c2f33dbcc0f4ed38056d8372e65ed73
Source dataset
uspto-grants-2014_10
Patent number
US08871770B2

Reaction notes

Loading…