Trifluoroacetic acid → HCID 86727668, compound

HRID 1749683Notes

Reaction equation

HRID 1749683 reaction equation
C(O)(C(F)(F)F)=O.[NH2:8][C:9]1[N:10]=[CH:11][C:12]([C:24]2[N:28]([CH2:29][CH3:30])[N:27]=[C:26]([CH:31]3[CH2:36][CH2:35][N:34](C(OC(C)(C)C)=O)[CH2:33][CH2:32]3)[N:25]=2)=[N:13][C:14]=1[C:15]1[O:16][C:17]([C:20]([CH3:23])([CH3:22])[CH3:21])=[N:18][N:19]=1>C(Cl)Cl>[C:20]([C:17]1[O:16][C:15]([C:14]2[C:9]([NH2:8])=[N:10][CH:11]=[C:12]([C:24]3[N:28]([CH2:29][CH3:30])[N:27]=[C:26]([CH:31]4[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]4)[N:25]=3)[N:13]=2)=[N:19][N:18]=1)([CH3:21])([CH3:22])[CH3:23]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86727667tert-butyl 4-(5-(5-amino-6-(5-tert-butyl-1,3,4-oxadiazol-2-yl)pyrazin-2-yl)-1-ethyl-1H-1,2,4-triazol-3-yl)piperidine-1-carboxylate

Product 1

HCID 86727668HCID 86727668, compoundYield 100.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (400 mL) was added portionwise to a solution of tert-butyl 4-(5-(5-amino-6-(5-tert-butyl-1,3,4-oxadiazol-2-yl)pyrazin-2-yl)-1-ethyl-1H-1,2,4-triazol-3-yl)piperidine-1-carboxylate (126 g, 253.22 mmol) in DCM (400 mL). The mixture was stirred for 16 hours at room temperature. The mixture was concentrated under reduced pressure, dissolved in DCM (1 L) and added slowly to a vigorously stirred solution of concentrated aqueous ammonia (500 mL) in water at 0° C. The organic solution was separated from the aqueous and concentrated under reduced pressure* to afford 3-(5-tert-butyl-1,3,4-oxadiazol-2-yl)-5-(1-ethyl-3-(piperidin-4-yl)-1H-1,2,4-triazol-5-yl)pyrazin-2-amine (101 g, 100%) as a yellow solid: 1H NMR Spectrum: (DMSO-d6) 1.4-1.52 (12H, m), 1.57-1.73 (2H, m), 1.83-1.93 (2H, m), 2.57-2.7 (2H, m), 2.71-2.84 (1H, m), 2.96-3.09 (2H, m), 4.58 (2H, q), 8.06 (2H, s), 8.84 (1H, s); Mass Spectrum [M+H]+=398.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. dissolutiondissolved in DCM (1 L)
  3. additionadded slowly to a vigorously stirred solution of concentrated aqueous ammonia (500 mL) in water at 0° C
  4. customThe organic solution was separated from the aqueous and
  5. concentrationconcentrated under reduced pressure*

Sources & evidence

ORD record
ord-2c01631d67da49b7946489b481a1b852
Source dataset
uspto-grants-2015_10
Patent number
US09156831B2

Reaction notes

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