Trifluoroacetic acid → HCID 86696365, compound

HRID 870666Notes

Reaction equation

HRID 870666 reaction equation
COC1C=C(OC)C=CC=1C[NH:6][C:7]([C:9]1[S:10][C:11]([C:14]2[N:18]3[N:19]=[C:20]([NH:23][CH2:24][CH2:25][CH2:26][N:27]4[CH2:31][CH2:30][CH2:29][C:28]4=[O:32])[CH:21]=[CH:22][C:17]3=[N:16][CH:15]=2)=[CH:12][CH:13]=1)=[O:8].C(O)(C(F)(F)F)=O>C(Cl)Cl>[O:32]=[C:28]1[CH2:29][CH2:30][CH2:31][N:27]1[CH2:26][CH2:25][CH2:24][NH:23][C:20]1[CH:21]=[CH:22][C:17]2[N:18]([C:14]([C:11]3[S:10][C:9]([C:7]([NH2:6])=[O:8])=[CH:13][CH:12]=3)=[CH:15][N:16]=2)[N:19]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86696366HCID 86696366, compound

Product 1

HCID 86696365HCID 86696365, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 50 mg (0.094 mmol) of N-(2,4-dimethoxybenzyl)-5-(6-((3-(2-oxopyrrolidin-1-yl)propyl)amino)imidazo[1,2-b]pyridazin-3-yl)thiophene-2-carboxamide dissolved in 1 mL DCM was added 5 mL of TFA. The resulting solvent was stirred at rt for 0.5 hr and then concentrated. It was purified in the PREP HPLC to obtain 26 mg (72%) of the desired product. 1H NMR (400 MHz, METHANOL-d4) δ ppm 2.04 (quin, J=7.39 Hz, 4H) 2.33-2.41 (m, 2H) 3.45-3.60 (m, 6H) 6.76 (d, J=9.85 Hz, 1H) 7.64-7.72 (m, 2H) 7.75 (d, J=4.04 Hz, 1H) 7.94 (s, 1H); LRMS (ESI) m/e 385.0 [(M+H)+, calcd for C18H20N6O2S 384.0].

Workup

  1. concentrationconcentrated
  2. customIt was purified in the PREP HPLC

Sources & evidence

ORD record
ord-1fc6a4f9f7524f249ed6fef6c25e895f
Source dataset
uspto-grants-2015_03
Patent number
US08969565B2

Reaction notes

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