Dichloromethane → HCID 86707533, compound

HRID 339043Notes

Reaction equation

HRID 339043 reaction equation
[Si]([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:14]=[C:15]([F:50])[CH:16]=[C:17]2[C:22]=1[N:21]=[C:20]([C:23]1[N:27]3[CH:28]=[C:29]([C@@H:32]([N:37]4[CH2:41][CH2:40][C@H:39]([NH:42]C(=O)OC(C)(C)C)[CH2:38]4)[C:33]([F:36])([F:35])[F:34])[CH:30]=[CH:31][C:26]3=[N:25][N:24]=1)[CH:19]=[CH:18]2)(C(C)(C)C)(C)C.[Cl:51]CCl>FC(F)(F)C(O)=O>[ClH:51].[ClH:51].[NH2:42][C@H:39]1[CH2:40][CH2:41][N:37]([C@H:32]([C:29]2[CH:30]=[CH:31][C:26]3[N:27]([C:23]([C:20]4[CH:19]=[CH:18][C:17]5[C:22](=[C:13]([O:12][CH2:11][CH2:10][CH2:9][OH:8])[CH:14]=[C:15]([F:50])[CH:16]=5)[N:21]=4)=[N:24][N:25]=3)[CH:28]=2)[C:33]([F:35])([F:34])[F:36])[CH2:38]1

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 86707534HCID 86707534, compound

Product 1

HCID 86707533HCID 86707533, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of tert-butyl (S)-1-((R)-1-(3-(8-(3-(tert-butyldimethyl silyloxy)propoxy)-6-fluoroquinolin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-2,2,2-trifluoroethyl)pyrrolidin-3-ylcarbamate (0.18 g, 0.24 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 purified by reverse phase chromatography on a C18 column (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 (0.12 g, 84%). FIA-MS APCI (+) m/z 505 (M+H).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customThe residue was purified by reverse phase chromatography on a C18 column (0-80% acetonitrile/water)
  3. customThe material isolated
  4. customafter purification
  5. dissolutionwas dissolved in methanol (0.5 mL)
  6. additionadded dropwise to hydrochloric acid (2M in diethyl ether; 5 mL)
  7. filtrationThe resulting salt was collected by vacuum filtration

Sources & evidence

ORD record
ord-d2df73bbfe024abb9333b077b63de498
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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