Hydrochloric Acid → n-(Piperidin-4-yl)-7-(1-(4-(trifluoromethyl)phenyl)piperidin-4-yloxy)imidazo[1,2-a]pyridine-2-carboxamide dihydrochloride salt

HRID 530944Notes

Reaction equation

HRID 530944 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:21]=[CH:20][N:19]4[CH:22]=[C:23]([C:25]([NH:27][CH:28]5[CH2:33][CH2:32][N:31](C(OC(C)(C)C)=O)[CH2:30][CH2:29]5)=[O:26])[N:24]=[C:18]4[CH:17]=3)[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.[ClH:43]>O1CCOCC1>[ClH:43].[ClH:43].[NH:31]1[CH2:30][CH2:29][CH:28]([NH:27][C:25]([C:23]2[N:24]=[C:18]3[CH:17]=[C:16]([O:15][CH:12]4[CH2:13][CH2:14][N:9]([C:6]5[CH:7]=[CH:8][C:3]([C:2]([F:1])([F:41])[F:42])=[CH:4][CH:5]=5)[CH2:10][CH2:11]4)[CH:21]=[CH:20][N:19]3[CH:22]=2)=[O:26])[CH2:33][CH2:32]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57951074Tert-butyl 4-(7-(1-(4-(trifluoromethyl)phenyl)piperidin-4-yloxy)imidazo[1,2-a]pyridine-2-carboxamido)piperidine-1-carboxylate

Product 1

HCID 69011101n-(Piperidin-4-yl)-7-(1-(4-(trifluoromethyl)phenyl)piperidin-4-yloxy)imidazo[1,2-a]pyridine-2-carboxamide dihydrochloride saltYield 98%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of tert-butyl 4-(7-(1-(4-(trifluoromethyl)phenyl)piperidin-4-yloxy)imidazo[1,2-a]pyridine-2-carboxamido)piperidine-1-carboxylate (0.13 g, 0.22 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)-7-(1-(4-(trifluoromethyl)phenyl)piperidin-4-yloxy)imidazo[1,2-a]pyridine-2-carboxamide dihydrochloride salt as a brown solid (0.13 g, 98%). 1H NMR (CD3OD, 300 MHz) δ 8.72 (m, 1H), 8.56 (m, 1H), 7.64 (m, 2H), 7.45 (m, 2H), 7.31 (m, 1H), 7.26 (m, 1H), 4.97 (m, 1H), 3.64 (m, 5H), 3.01 (m, 2H), 2.14 (m, 10H) ppm; MS (ES) 488.1 (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-1aeebc7ef54141bb8a00f4fafefb7f13
Source dataset
uspto-grants-2016_05
Patent number
US09353111B2

Reaction notes

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