Acetonitrile → Trifluoroacetic acid

HRID 912533Notes

Reaction equation

HRID 912533 reaction equation
[C:1]([C:3]1[C:8]2[N:9]=[CH:10][N:11]([CH3:12])[C:7]=2[CH:6]=[C:5]([C:13]2[CH:35]=[CH:34][C:16]([O:17][CH2:18][CH2:19][C:20]3([F:33])[CH2:25][CH2:24][N:23](C(OC(C)(C)C)=O)[CH2:22][CH2:21]3)=[C:15]([C:36]([F:39])([F:38])[F:37])[CH:14]=2)[N:4]=1)#[N:2].C(#N)C.[F:43][C:44]([F:49])([F:48])[C:45]([OH:47])=[O:46].C(Cl)[Cl:51]>>[ClH:51].[F:33][C:20]1([CH2:19][CH2:18][O:17][C:16]2[CH:34]=[CH:35][C:13]([C:5]3[N:4]=[C:3]([C:1]#[N:2])[C:8]4[N:9]=[CH:10][N:11]([CH3:12])[C:7]=4[CH:6]=3)=[CH:14][C:15]=2[C:36]([F:37])([F:38])[F:39])[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1.[C:45]([OH:47])([C:44]([F:49])([F:48])[F:43])=[O:46]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 59410680HCID 59410680, compound

Product 2

HCID 6422Trifluoroacetic acidHCID 67145137HCID 67145137, compound

Procedure

To tert-butyl 4-(2-(4-(4-cyano-1-methyl-1H-imidazo[4,5-c]pyridin-6-yl)-2-(trifluoromethyl)phenoxy)ethyl)-4-fluoropiperidine-1-carboxylate (0.7 g) in DCM (15 ml) was added acetonitrile (10 ml), followed by trifluoroacetic acid (10 ml). The mixture was stirred at room temperature for 10 minutes, then solvent and excess TFA were removed under vacuum. The residue was taken into ethyl acetate (15 ml), and diethylether (20 ml) was then added. The white precipitate product was then collected by filtration to give desired product as a TFA salt (0.7 g). 50 mg of this TFA salt was then converted to free base by means of SCX, then to HCl salt by treating with 2M HCl in ether. 1H NMR (CD3OD) δ: 8.60 (s, 1H), 8.45 (s, 1H), 8.41 (s, 1H), 8.40 (d, 1H), 7.39 (d, 1H), 4.40 (t, 2H), 4.05 (s, 3H), 3.2-3.5 (m, 4H), 2.2-2.4 (m, 4H), 2.0-2.2 (m, 2H). MS m/z 448 (M+H).

Workup

  1. customsolvent and excess TFA were removed under vacuum
  2. additionwas then added
  3. filtrationThe white precipitate product was then collected by filtration

Sources & evidence

ORD record
ord-dd7bd0cee4344bb2abecfe0e291da5a8
Source dataset
uspto-grants-2011_09
Patent number
US08026236B2

Reaction notes

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