Trifluoroacetic acid → HCID 66970554, compound

HRID 1363148Notes

Reaction equation

HRID 1363148 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[N:10]=[CH:9][N:8]([C:11]3[N:16]=[C:15]4[N:17]([C@@H:28]([C:30]5[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=5)[CH3:29])[C:18](=[O:27])[N:19](C(OC(C)(C)C)=O)[C:14]4=[CH:13][CH:12]=3)[C:7]=2[CH:36]=1)#[N:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[O:27]=[C:18]1[N:17]([C@@H:28]([C:30]2[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=2)[CH3:29])[C:15]2=[N:16][C:11]([N:8]3[C:7]4[CH:36]=[C:3]([C:1]#[N:2])[CH:4]=[CH:5][C:6]=4[N:10]=[CH:9]3)=[CH:12][CH:13]=[C:14]2[NH:19]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66970649HCID 66970649, compound

Product 1

HCID 66970554HCID 66970554, compoundYield 86.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl 5-(6-cyano-1H-benzo[d]imidazol-1-yl)-2-oxo-3-((R)-1-(pyridin-3-yl)ethyl)-2,3-dihydroimidazo[4,5-b]pyridine-1-carboxylate (72) (57 mg) in methylene chloride (1 mL) was treated with TFA (1 mL) for one hour. The mixture was concentrated and the resulting TFA salt was converted to the HCl salt by dissolving it in 5 mL EtOH and adding 0.5 mL of conc. HCl, then concentrating the solution in vacuo. The process was repeated and the resulting residue was dissolved in a minimum amount of methanol and triturated with the addition of ethyl ether. After 3 triturations, 3-(2-oxo-3-((R)-1-(pyridin-3-yl)ethyl)-2,3-dihydro-1H-imidazo[4,5-b]pyridin-5-yl)-3H-benzo[d]imidazole-5-carbonitrile (73) HCl salt (39 mg) was isolated as a tan colored solid: 1H-NMR (CD3OD) δ 9.9 (br s, 1H), 9.2 (s, 1H), 9.0 (m, 2H), 8.5 (s, 1H), 8.3 (m, 1H), 8.2 (m, 1H), 8.1 (d, 1H), 7.9 (d, 1H), 7.8 (d, 1H), 6.3 (q, 1H), 2.3 (d, 3H).

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutionby dissolving it in 5 mL EtOH
  3. additionadding 0.5 mL of conc. HCl
  4. concentrationconcentrating the solution in vacuo
  5. dissolutionthe resulting residue was dissolved in a minimum amount of methanol
  6. customtriturated with the addition of ethyl ether

Sources & evidence

ORD record
ord-68f3739e3f7c4241bc71a6b0b41e2621
Source dataset
uspto-grants-2011_02
Patent number
US07884109B2

Reaction notes

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