Trifluoroacetic acid → HCID 58299893, compound

HRID 876045Notes

Reaction equation

HRID 876045 reaction equation
[C:1]1([N:7]2[C:11]3[CH:12]=[N:13][CH:14]=[CH:15][C:10]=3[C:9]3[CH:16]=[N:17][C:18]([NH:20][C:21]4[N:26]=[CH:25][C:24]([N:27]5[CH2:32][CH2:31][N:30](C(OC(C)(C)C)=O)[CH2:29][CH2:28]5)=[CH:23][CH:22]=4)=[CH:19][C:8]2=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[C:1]1([N:7]2[C:11]3[CH:12]=[N:13][CH:14]=[CH:15][C:10]=3[C:9]3[CH:16]=[N:17][C:18]([NH:20][C:21]4[CH:22]=[CH:23][C:24]([N:27]5[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]5)=[CH:25][N:26]=4)=[CH:19][C:8]2=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58300169tert-Butyl 4-(6-((5-phenyl-5 H-pyrido[3',4':4,5]pyrrolo[2,3-c]pyridin-3-yl)amino)-3-pyridinyl)-1-piperazinecarboxylate

Product 1

HCID 58299893HCID 58299893, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of crude compound 372 in DCM (8 mL) was treated with trifluoroacetic acid (2.0 mL, 27 mmol) at room temperature for 2 h. After the volatiles were removed, the residue was subjected to reverse phase preparative HPLC (acetonitrile/H2O containing 0.1% TFA each, 40 min from 10 to 40%). Lyophilization provided compound 370 (12 mg) as a yellow solid (TFA salt). 1H NMR (500 MHz, CD3OD) δ ppm 9.46 (1 H, s), 8.80 (1 H, d, J=0.7 Hz), 8.65 (1 H, d, J=5.6 Hz), 8.53 (1 H, d, J=5.6 Hz), 8.05 (1 H, d, J=2.9 Hz), 7.90 (1 H, dd, J=9.3, 2.9 Hz), 7.77-7.83 (2 H, m), 7.68-7.76 (3 H, m), 7.24 (1 H, d, J=9.3 Hz), 7.14 (1 H, s), 3.46-3.53 (4 H, m), 3.40-3.46 (4 H, m). LCMS-ESI (POS), M/Z, M+1. Found 422.2.

Workup

  1. customAfter the volatiles were removed
  2. custom40 min

Sources & evidence

ORD record
ord-8abffcadeef64ee4b760e49d3e0dac7f
Source dataset
uspto-grants-2015_03
Patent number
US08980903B2

Reaction notes

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