Hydrochloric Acid → HCID 66884421, compound

HRID 539833Notes

Reaction equation

HRID 539833 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-c4c01ec6e8b14a12b990d24e26c9038b
Source dataset
uspto-grants-2014_10
Patent number
US08871770B2

Reaction notes

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