Hydrochloric Acid → HCID 66884421, compound

HRID 1773462Notes

Reaction equation

HRID 1773462 reaction equation
[F:1][C:2]([F:39])([F:38])[C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][CH:12]([O:15][C:16]3[N:17]=[CH:18][C:19]([C:22]([NH:24][CH:25]4[CH2:30][CH2:29][N:28](C(OC(C)(C)C)=O)[CH2:27][CH2:26]4)=[O:23])=[N:20][CH:21]=3)[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.[ClH:40]>O1CCOCC1>[ClH:40].[ClH:40].[NH:28]1[CH2:29][CH2:30][CH:25]([NH:24][C:22]([C:19]2[CH:18]=[N:17][C:16]([O:15][CH:12]3[CH2:11][CH2:10][N:9]([C:6]4[CH:7]=[CH:8][C:3]([C:2]([F:39])([F:1])[F:38])=[CH:4][CH:5]=4)[CH2:14][CH2:13]3)=[CH:21][N:20]=2)=[O:23])[CH2:26][CH2:27]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57951070HCID 57951070, compound

Product 1

HCID 66884421HCID 66884421, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of tert-butyl 4-(5-(1-(4-(trifluoromethyl)phenyl)piperidin-4-yloxy)pyrazine-2-carboxamido)piperidine-1-carboxylate (0.06 g, 0.11 mmol) and 4N hydrochloric acid in dioxane (1 mL) was stirred at room temperature for 0.5 h. The reaction mixture was concentrated and washed with diethyl ether (2×1 mL) and then dried under reduced pressure to afford N-(piperidin-4-yl)-5-(1-(4-(trifluoromethyl)phenyl)piperidin-4-yloxy)pyrazine-2-carboxamide dihydrochloride salt (compound 20) as a brown solid (0.56 g, 99%). 1H NMR (CD3OD, 300 MHz) δ 8.80 (s, 1H), 8.25 (s, 5H), 7.59 (m, 2H), 7.28 (m, 2H), 5.44 (m, 1H), 4.18 (m, 1H), 3.55 (m, 4H), 3.77 (m, 2H), 3.42 (m, 4H), 3.15 (m, 2H), 2.07 (m, 8H) ppm; MS (ES) 450.5 (M+1).

Workup

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

Sources & evidence

ORD record
ord-41b292a3a78f40bf98c8b3037f7bb57b
Source dataset
uspto-grants-2016_02
Patent number
US09255085B2

Reaction notes

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