Trifluoroacetic acid → (2-Aminopyridin-3-yl)(3-(piperazin-1-yl)isoquinolin-1-yl)methanone bis(2,2,2-trifluoroacetate)

HRID 401504Notes

Reaction equation

HRID 401504 reaction equation
[NH2:1][C:2]1[N:32]=[CH:31][CH:30]=[CH:29][C:3]=1[C:4]([C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[C:8]([N:16]2[CH2:21][CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18][CH2:17]2)[N:7]=1)=[O:5].[F:33][C:34]([F:39])([F:38])[C:35]([OH:37])=[O:36]>ClCCl>[F:33][C:34]([F:39])([F:38])[C:35]([OH:37])=[O:36].[F:33][C:34]([F:39])([F:38])[C:35]([OH:37])=[O:36].[NH2:1][C:2]1[C:3]([C:4]([C:6]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=[C:8]([N:16]3[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]3)[N:7]=2)=[O:5])=[CH:29][CH:30]=[CH:31][N:32]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57690535Tert-butyl 4-(1-(2-aminonicotinoyl)isoquinolin-3-yl)piperazine-carboxylate

Product 1

HCID 86630216(2-Aminopyridin-3-yl)(3-(piperazin-1-yl)isoquinolin-1-yl)methanone bis(2,2,2-trifluoroacetate)Yield 26%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-(1-(2-aminonicotinoyl)isoquinolin-3-yl)piperazine-1-carboxylate (6 mg, 0.014 mmol) in dichloromethane (2 ml) was added trifluoroacetic acid (0.5 ml). The solution was stirred at room temperature for 1 hour. The resulting mixture was concentrated in vacuo and triturated twice with ether and dried to leave the compound as an orange solid (2 mg, 26% yield).

Workup

  1. concentrationThe resulting mixture was concentrated in vacuo
  2. customtriturated twice with ether
  3. customdried

Sources & evidence

ORD record
ord-7b8235fe677b4a3aa22ddf87b7fb0e26
Source dataset
uspto-grants-2014_06
Patent number
US08741931B2

Reaction notes

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