Trifluoroacetic acid → Trifluoroacetic acid

HRID 2239854Notes

Reaction equation

HRID 2239854 reaction equation
FC1C=CC(C2[C:13](=[O:14])[C:12]([C:15]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([NH:24][C:25]4[C:26]5[N:27]([CH:46]=[CH:47][N:48]=5)[N:28]=[C:29]([NH:31][C@H:32]5[CH2:37][CH2:36][C@H:35]([NH:38]C(=O)OC(C)(C)C)[CH2:34][CH2:33]5)[CH:30]=4)=[CH:20][CH:19]=3)=[O:16])=[CH:11][CH:10]=[CH:9]2)=CC=1.[F:49][C:50]([F:55])([F:54])[C:51]([OH:53])=[O:52]>C(Cl)Cl>[NH2:38][C@H:35]1[CH2:34][CH2:33][C@H:32]([NH:31][C:29]2[CH:30]=[C:25]([NH:24][C:21]3[CH:20]=[CH:19][C:18]([NH:17][C:15]([C:12]4[C:13](=[O:14])[N:17]([C:18]5[CH:19]=[CH:20][C:50]([F:55])=[CH:51][CH:23]=5)[CH:9]=[CH:10][CH:11]=4)=[O:16])=[CH:23][CH:22]=3)[C:26]3[N:27]([CH:46]=[CH:47][N:48]=3)[N:28]=2)[CH2:37][CH2:36]1.[C:51]([OH:53])([C:50]([F:55])([F:54])[F:49])=[O:52]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178454004HCID 178454004, compound

Product 2

HCID 6422Trifluoroacetic acidHCID 178511632HCID 178511632, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a 50 ml round bottom flask added tert-butyl(trans)-4-(8-(4-(5-(4-fluorophenyl)-6-oxocyclohexa-1,3-dienecarboxamido)phenylamino)imidazo[1,2-b]pyridazin-6-ylamino)cyclohexylcarbamate (0.025 g, 0.04 mmol) from 1e and 20% trifloroacetic acid in methylene chloride (4 ml). The reaction was allowed to stir at room temperature for 5 min. The reaction was then concentrated in vacuo and diluted with methanol and purified via HPLC (20-100% methanol gradient), which provided the titled compound as a TFA salt (0.007 g). 1H NMR (400 MHz, MeOD) δ ppm 12.11 (1H, s), 8.68 (1H, dd, J=7.38, 2.29 Hz), 7.87-8.13 (2H, m), 7.71-7.88 (3H, m), 7.41-7.63 (2H, m), 7.33 (4H, t, J=8.65 Hz), 6.65-6.82 (1H, m), 6.43 (1H, s), 3.54-3.88 (1H, m), 2.96-3.17 (1H, m), 2.23 (2H, m), 2.08 (2H, m), 1.44-1.68 (2H, m), 1.17-1.43 (2H, m). LC/MS, m/e 553 (M+1). HPLC Rt, 2.14 min. YMC ODSC18 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 was then concentrated in vacuo
  2. additiondiluted with methanol
  3. custompurified via HPLC (20-100% methanol gradient), which

Sources & evidence

ORD record
ord-eb42d9aaf8d649308c77d1b4c1077292
Source dataset
uspto-grants-2010_05
Patent number
US07723336B2

Reaction notes

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