Trifluoroacetic acid → Trifluoroacetic acid

HRID 2239837Notes

Reaction equation

HRID 2239837 reaction equation
[C:1]1([NH:7][C:8](=[O:34])[NH:9][C:10]2[C:11]3[N:12]([CH:31]=[CH:32][N:33]=3)[N:13]=[C:14]([NH:16][C@H:17]3[CH2:22][CH2:21][C@H:20]([NH:23]C(=O)OC(C)(C)C)[CH2:19][CH2:18]3)[CH:15]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:35]([OH:41])([C:37]([F:40])([F:39])[F:38])=[O:36]>ClCCl>[NH2:23][C@H:20]1[CH2:21][CH2:22][C@H:17]([NH:16][C:14]2[CH:15]=[C:10]([NH:9][C:8]([NH:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[O:34])[C:11]3[N:12]([CH:31]=[CH:32][N:33]=3)[N:13]=2)[CH2:18][CH2:19]1.[C:35]([OH:41])([C:37]([F:40])([F:39])[F:38])=[O:36]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178454007HCID 178454007, compound

Product 2

HCID 6422Trifluoroacetic acidYield 64%HCID 178511642HCID 178511642, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To tert-butyl(trans)-4-(8-(3-phenylureido)imidazo[1,2-b]pyridazin-6-ylamino)cyclohexylcarbamate (6.3 mg, 0.135 mmol) from 1a in dichloromethane (2 mL) was added TFA (1 mL). After stirring at RT for 2 hours, the reaction solution was concentrated in vacuo. The residue was purified by SCX column (300 mg, eluting with 2M ammonia in methanol) to give the title compound as a TFA salt 3.2 mgs (64%). 1H NMR (500 MHz, MeOH) δ ppm 7.64 (1H, s), 7.47 (2H, m), 7.31 (2H, m), 7.06 (2H, m), 6.71 (2H, m), 3.63 (1H, m), 2.71 (1H, m), 2.15 (2H, m), 1.91 (2H, m), 1.28-1.33 (4H, t). LC/MS, m/e 366.27 (M+1). HPLC Rt, 2.18 min. Waters Sunfire C18 column (4.6×50 mm). 0%-100% B. Solvent B: (90% MeOH, 10% H2O, 0.1% TFA). Solvent A: (10% MeOH, 90% H2O, 0.1% TFA). Gradient, start % B=0, final % B=100, gradient time 4 min, hold at 100% B 1 min, flow rate 4 mL/min.

Workup

  1. concentrationthe reaction solution was concentrated in vacuo
  2. customThe residue was purified by SCX column (300 mg, eluting with 2M ammonia in methanol)

Sources & evidence

ORD record
ord-73e2e140672445c59b3ca30fa2a1f02c
Source dataset
uspto-grants-2010_05
Patent number
US07723336B2

Reaction notes

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