Trifluoroacetic acid → HCID 67959784, compound

HRID 1529364Notes

Reaction equation

HRID 1529364 reaction equation
C(OC([NH:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]2[N:20]=[C:19]([C:21]3[C:29]4[C:24](=[CH:25][CH:26]=[C:27]([C:30]([O:32][CH3:33])=[O:31])[CH:28]=4)[N:23](C(OC(C)(C)C)=O)[CH:22]=3)[CH:18]=[N:17][CH:16]=2)[CH2:11][CH2:10]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)(Cl)Cl>[NH2:8][CH:9]1[CH2:10][CH2:11][N:12]([C:15]2[N:20]=[C:19]([C:21]3[C:29]4[C:24](=[CH:25][CH:26]=[C:27]([C:30]([O:32][CH3:33])=[O:31])[CH:28]=4)[NH:23][CH:22]=3)[CH:18]=[N:17][CH:16]=2)[CH2:13][CH2:14]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67959959HCID 67959959, compound

Product 1

HCID 67959784HCID 67959784, compoundYield 48.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of 1-tert-butyl 5-methyl 3-(6-(4-(tert-butoxycarbonylamino)piperidin-1-yl)pyrazin-2-yl)-1H-indole-1,5-dicarboxylate (300 mg, 0.53 mmol) in chloroform (3.0 mL) was added TFA (3.0 mL) at 0° C. The reaction mixture was heated at 50° C. for 12 h. After removal of TFA the crude product was purified by preparative HPLC to obtain title compound (90 mg, 47%) as a brown solid. MS (ESI, pos. ion) m/z: 352.1 (M+1).

Workup

  1. customAfter removal of TFA the crude product
  2. customwas purified by preparative HPLC

Sources & evidence

ORD record
ord-1108b039607e43d884e46801913c9e41
Source dataset
uspto-grants-2015_07
Patent number
US09090593B2

Reaction notes

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