Dichloromethane → HCID 86707514, compound

HRID 339013Notes

Reaction equation

HRID 339013 reaction equation
[F:1][C:2]([F:42])([F:41])[C@H:3]([N:28]1[CH2:32][CH2:31][C@H:30]([NH:33]C(=O)OC(C)(C)C)[CH2:29]1)[C:4]1[CH:5]=[CH:6][C:7]2[N:8]([C:10]([C:13]3[CH:22]=[CH:21][C:20]4[C:15](=[C:16]([O:23][CH2:24][C@@H:25]([OH:27])[CH3:26])[CH:17]=[CH:18][CH:19]=4)[N:14]=3)=[N:11][N:12]=2)[CH:9]=1.[Cl:43]CCl>FC(F)(F)C(O)=O>[ClH:43].[ClH:43].[NH2:33][C@H:30]1[CH2:31][CH2:32][N:28]([C@H:3]([C:4]2[CH:5]=[CH:6][C:7]3[N:8]([C:10]([C:13]4[CH:22]=[CH:21][C:20]5[C:15](=[C:16]([O:23][CH2:24][C@@H:25]([OH:27])[CH3:26])[CH:17]=[CH:18][CH:19]=5)[N:14]=4)=[N:11][N:12]=3)[CH:9]=2)[C:2]([F:41])([F:42])[F:1])[CH2:29]1

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 86707513HCID 86707513, compound

Product 1

HCID 86707514HCID 86707514, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of tert-butyl (S)-1-((R)-2,2,2-trifluoro-1-(3-(8-((S)-2-hydroxypropoxy)quinolin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)ethyl)pyrrolidin-3-ylcarbamate (0.11 g, 0.19 mmol) in dichloromethane (1 mL) and trifluoroacetic acid (2 mL) was stirred at ambient temperature for 30 minutes. The reaction mixture was concentrated under reduced pressure. The residue was by reverse phase chromatography on C18 (0-80% acetonitrile/water). The material isolated after purification was dissolved in methanol (0.5 mL) and added dropwise to hydrochloric acid (2M in diethyl ether; 5 mL). The resulting salt was collected by vacuum filtration to provide the title compound (0.026 g, 25%). LCMS APCI (+) m/z 487 (M+H).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customThe material isolated
  3. customafter purification
  4. dissolutionwas dissolved in methanol (0.5 mL)
  5. additionadded dropwise to hydrochloric acid (2M in diethyl ether; 5 mL)
  6. filtrationThe resulting salt was collected by vacuum filtration

Sources & evidence

ORD record
ord-03585429b9644e7a903aa4f32893ebef
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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