Trifluoroacetic acid → HCID 86707096, compound

HRID 57903Notes

Reaction equation

HRID 57903 reaction equation
[C:1]([C:3]1[C:4]([N:25]2[CH2:30][CH2:29][CH2:28][C@H:27]([NH:31]C(=O)OC(C)(C)C)[CH2:26]2)=[N:5][C:6]([N:9]2[C:17]3[CH:16]=[C:15]([C:18]4[CH:23]=[N:22][CH:21]=[C:20]([CH3:24])[N:19]=4)[N:14]=[CH:13][C:12]=3[CH:11]=[N:10]2)=[CH:7][CH:8]=1)#[N:2].C(O)(C(F)(F)F)=O>ClCCl>[NH2:31][C@H:27]1[CH2:28][CH2:29][CH2:30][N:25]([C:4]2[N:5]=[C:6]([N:9]3[C:17]4[CH:16]=[C:15]([C:18]5[CH:23]=[N:22][CH:21]=[C:20]([CH3:24])[N:19]=5)[N:14]=[CH:13][C:12]=4[CH:11]=[N:10]3)[CH:7]=[CH:8][C:3]=2[C:1]#[N:2])[CH2:26]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86707094tert-butyl N-[(3S)-1-[3-cyano-6-[6-(6-methylpyrazin-2-yl)pyrazolo[4,3-c]pyridin-1-yl]-2-pyridyl]-3-piperidyl]carbamate

Product 1

HCID 86707096HCID 86707096, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl N-[(3S)-1-[3-cyano-6-[6-(6-methylpyrazin-2-yl)pyrazolo[4,3-c]pyridin-1-yl]-2-pyridyl]-3-piperidyl]carbamate (0.4859 mmol; 248.6 mg) in dichloromethane (8 mL) was added TFA (2 mL). The resulting mixture was stirred at room temperature for 4 hours. The mixture was concentrated and the residue was purified by reverse phase HPLC to afford 201 was obtained as an off-white solid (361.6 mg, 18%). 1H NMR (400 MHz, DMSO) δ 9.61-9.55 (s, 1H), 9.48-9.44 (s, 1H), 9.37-9.33 (s, 1H), 8.80-8.75 (s, 1H), 8.66-8.62 (s, 1H), 8.26-8.19 (m, 2H), 7.48-7.44 (d, J=8.4 Hz, 1H), 4.29-4.19 (dd, J=10.7, 6.9 Hz, 2H), 3.00-2.94 (m, 1H), 2.66-2.62 (s, 3H), 2.03-1.89 (dd, J=18.5, 10.2 Hz, 2H), 1.80-1.66 (m, 1H), 1.49-1.37 (m, 1H); MS (ESI) m/z: 412.2 [M+H]+

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-d626435319104a2d90667005a2df5ebc
Source dataset
uspto-grants-2016_09
Patent number
US09434725B2

Reaction notes

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