Trifluoroacetic acid → HCID 86727668, compound

HRID 1749047Notes

Reaction equation

HRID 1749047 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:17]2[N:21]([CH2:22][CH3:23])[N:20]=[C:19]([CH:24]3[CH2:29][CH2:28][N:27](C(OC(C)(C)C)=O)[CH2:26][CH2:25]3)[N:18]=2)=[N:6][C:7]=1[C:8]1[O:9][C:10]([C:13]([CH3:16])([CH3:15])[CH3:14])=[N:11][N:12]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:13]([C:10]1[O:9][C:8]([C:7]2[C:2]([NH2:1])=[N:3][CH:4]=[C:5]([C:17]3[N:21]([CH2:22][CH3:23])[N:20]=[C:19]([CH:24]4[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]4)[N:18]=3)[N:6]=2)=[N:12][N:11]=1)([CH3:14])([CH3:15])[CH3:16]

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, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
7.5 °C

Procedure

A suspension 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 (3009.5 g, 6.05 mol) in DCM (9 L) was cooled to 5-10° C. under N2. TFA (9 L) was added portionwise to the suspension whilst maintaining the temperature <30° C. The reaction mixture was stirred at room temperature for 1 h. The mixture was concentrated, the resulting residue was dissolved in water (30 L) and added slowly to a 35% aqueous ammonia solution (12 L) at 0-5° C. The suspension was stirred for 30 min then the product was filtered off and washed with water (2×6 L). The product was dried at 50° C. in vacuo for 2 days 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 ((2496 g): 1H NMR Spectrum: (DMSO-d6) 1.4-1.52 (12H, m), 1.57-1.73 (2H, m), 1.83-1.93 (2H, nm), 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. temperaturewhilst maintaining the temperature <30° C
  2. concentrationThe mixture was concentrated
  3. dissolutionthe resulting residue was dissolved in water (30 L)
  4. additionadded slowly to a 35% aqueous ammonia solution (12 L) at 0-5° C
  5. stirringThe suspension was stirred for 30 min
  6. filtrationthe product was filtered off
  7. washwashed with water (2×6 L)
  8. customThe product was dried at 50° C. in vacuo for 2 days

Sources & evidence

ORD record
ord-cba5ecfd038c475fb472aeaa9076d2d1
Source dataset
uspto-grants-2015_10
Patent number
US09155727B2

Reaction notes

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