Trifluoroacetic acid → HCID 67959787, compound

HRID 1529360Notes

Reaction equation

HRID 1529360 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]([NH:30][C:31](=[O:34])[CH2:32][CH3:33])[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>[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]([NH:30][C:31](=[O:34])[CH2:32][CH3:33])[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 67958305HCID 67958305, compound

Product 1

HCID 67959787HCID 67959787, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 3-(6-(4-(tert-butoxycarbonylamino)piperidin-1-yl)pyrazin-2-yl)-5-propionamido-1H-indole-1-carboxylate (200 mg, 0.35 mmol) in DCM (2 mL) was treated with TFA (2 mL) and stirred at RT for 12 h. The reaction mixture was quenched with water and neutralized with K2CO3. The resulting precipitate was filtered, washed with water and dried to obtain the crude product. The crude product was purified by prep HPLC (column: Zorbax Eclipse XDBC Prep C18 5 μm 21.2*150 mm; flow rate: 15.0 mL/min; mobile phase: A: 0.1% TFA in water. B: ACN+MeOH (1:1); gradient: % B, 10% to 50%) to N-(3-(6-(4-aminopiperidin-1-yl)pyrazin-2-yl)-1H-indol-5-yl)propionamide (234) (50 mg, 39%). MS (ESI, pos. ion) m/z: 413.2 (M+1).

Workup

  1. customThe reaction mixture was quenched with water and neutralized with K2CO3
  2. filtrationThe resulting precipitate was filtered
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-87378d674d4d49679d9c7fdbc3438b90
Source dataset
uspto-grants-2015_07
Patent number
US09090593B2

Reaction notes

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