Trifluoroacetic acid → 1-(6-(5-(2-chloro-6-fluorophenyl)-1H-indol-3-yl)pyrazin-2-yl)piperidin-4-amine bis(2,2,2-trifluoroacetate)

HRID 1529323Notes

Reaction equation

HRID 1529323 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH:13]=[C:12]2[C:18]1[N:23]=[C:22]([N:24]2[CH2:29][CH2:28][CH:27]([NH:30]C(=O)OC(C)(C)C)[CH2:26][CH2:25]2)[CH:21]=[N:20][CH:19]=1.[C:38]([OH:44])([C:40]([F:43])([F:42])[F:41])=[O:39]>C(Cl)Cl>[F:41][C:40]([F:43])([F:42])[C:38]([OH:44])=[O:39].[F:41][C:40]([F:43])([F:42])[C:38]([OH:44])=[O:39].[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH:13]=[C:12]2[C:18]1[N:23]=[C:22]([N:24]2[CH2:29][CH2:28][CH:27]([NH2:30])[CH2:26][CH2:25]2)[CH:21]=[N:20][CH:19]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 67959678tert-butyl 1-(6-(5-(2-chloro-6-fluorophenyl)-1H-indol-3-yl)pyrazin-2-yl)piperidin-4-ylcarbamate

Product 1

HCID 867097721-(6-(5-(2-chloro-6-fluorophenyl)-1H-indol-3-yl)pyrazin-2-yl)piperidin-4-amine bis(2,2,2-trifluoroacetate)

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl 1-(6-(5-(2-chloro-6-fluorophenyl)-1H-indol-3-yl)pyrazin-2-yl)piperidin-4-ylcarbamate (0.104 g, 0.199 mmol) in 2 mL DCM and TFA (0.153 mL, 1.992 mmol) was stirred for 1 h. Additional TFA (0.153 mL, 1.992 mmol) was added. After 1 h additional, the reaction was concentrated, and the material suspended in Et2O to give a solid. The solid was collected by filtration, and was dried in vacuo overnight, to give 1-(6-(5-(2-chloro-6-fluorophenyl)-1H-indol-3-yl)pyrazin-2-yl)piperidin-4-amine bis(2,2,2-trifluoroacetate) as a yellow solid. MS (ESI, pos. ion) m/z: 422 (M+1).

Workup

  1. concentrationthe reaction was concentrated
  2. customto give a solid
  3. filtrationThe solid was collected by filtration
  4. customwas dried in vacuo overnight

Sources & evidence

ORD record
ord-e83ccba7c00948d8bb5f876c9b5802ab
Source dataset
uspto-grants-2015_07
Patent number
US09090593B2

Reaction notes

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