Hydrochloric Acid → HCID 66884421, compound

HRID 530948Notes

Reaction equation

HRID 530948 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-4e9715959f8a41edbd87ecbf0f8db643
Source dataset
uspto-grants-2016_05
Patent number
US09353111B2

Reaction notes

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