Trifluoroacetic acid → HCID 18367784, compound

HRID 379884Notes

Reaction equation

HRID 379884 reaction equation
C(OC([NH:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]([C:15]([C:17]2[NH:18][C:19]3[C:24]([C:25]=2[NH:26][C:27](=[O:30])[CH2:28][CH3:29])=[CH:23][CH:22]=[C:21]([Cl:31])[CH:20]=3)=[O:16])[CH:10]=1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(=O)(O)[O-].[Na+]>[ClH:31].[NH2:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]([C:15]([C:17]2[NH:18][C:19]3[C:24]([C:25]=2[NH:26][C:27](=[O:30])[CH2:28][CH3:29])=[CH:23][CH:22]=[C:21]([Cl:31])[CH:20]=3)=[O:16])[CH:10]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 18368070HCID 18368070, compound

Product 1

HCID 18367784HCID 18367784, compound

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

2-[4-(tert-Butoxycarbonyl)aminopyridine-2-carbonyl]-6-chloro-3-(propionylamino)indole (step 4, 118 mg, 0.266 mmol) was treated with trifluoroacetic acid (4 ml) at room temperature for 1 h. The mixture was concentrated and azeotroped with toluene to give an oily residue. The residue was basified with saturated aqueous sodium bicarbonate (30 ml) and extracted with dichloromethane (30 ml×3). The organic phase was dried (K2CO3), and concentrated to afford the free base of title compound. The free base was dissolved in 10% HCl—MeOH (4 ml) and then evaporated. The residue obtained was crystallized from ethanol-diethyl ether to give the title compound. m.p.: 199-204° C. (decomposition) 1H-NMR (DMSO-d6) δ: 12.03 (1 H, br s), 10.41 (1 H, br s), 8.17 (1 H, d, J=7.3 Hz), 7.93 (1 H, d, J=8.9 Hz), 7.48 (1 H, d, J=1.6 Hz), 7.18 (1 H, dd, J=1.6, 8.7 Hz), 7.12 (1 H, d, J=1.8 Hz), 6.88 (1H, dd, J=7.4, 2.0 Hz), 2.18 (1 H, q, J=7.4 Hz), 0.82 (3 H, t, J=7.4 Hz).

Workup

  1. concentrationThe mixture was concentrated
  2. customazeotroped with toluene
  3. customto give an oily residue
  4. extractionextracted with dichloromethane (30 ml×3)
  5. dry with materialThe organic phase was dried (K2CO3)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-4fc83dd233a9423e8bc4e7eddb26a318
Source dataset
uspto-grants-2001_10
Patent number
US06300363B1

Reaction notes

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