Boron tribromide → HCID 178481999, compound

HRID 1960008Notes

Reaction equation

HRID 1960008 reaction equation
C([O:8][CH2:9][CH2:10][C@H:11]1[CH2:16][CH2:15][C@H:14]([C@H:17]2[CH2:21][CH2:20][CH2:19][N:18]2[C:22]2[C:31]([CH2:32][N:33]([C:49]3[N:50]=[N:51][N:52]([CH3:54])[N:53]=3)[CH2:34][C:35]3[CH:40]=[C:39]([C:41]([F:44])([F:43])[F:42])[CH:38]=[C:37]([C:45]([F:48])([F:47])[F:46])[CH:36]=3)=[CH:30][C:29]3[C:24](=[CH:25][C:26]([F:56])=[C:27]([F:55])[CH:28]=3)[N:23]=2)[CH2:13][CH2:12]1)C1C=CC=CC=1.B(Br)(Br)Br>C(Cl)Cl>[F:43][C:41]([F:42])([F:44])[C:39]1[CH:40]=[C:35]([CH:36]=[C:37]([C:45]([F:46])([F:47])[F:48])[CH:38]=1)[CH2:34][N:33]([CH2:32][C:31]1[C:22]([N:18]2[CH2:19][CH2:20][CH2:21][C@@H:17]2[C@H:14]2[CH2:13][CH2:12][C@H:11]([CH2:10][CH2:9][OH:8])[CH2:16][CH2:15]2)=[N:23][C:24]2[C:29]([CH:30]=1)=[CH:28][C:27]([F:55])=[C:26]([F:56])[CH:25]=2)[C:49]1[N:50]=[N:51][N:52]([CH3:54])[N:53]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 178482000HCID 178482000, compound

Product 1

HCID 178481999HCID 178481999, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of trans-N-[2-((R)-2-{4-[2-(benzyloxy)ethyl]cyclohexyl}pyrrolidin-1-yl)-6,7-difluoroquinolin-3-ylmethyl]-N-[3,5-bis(trifluoromethyl)benzyl](2-methyl-2H-tetrazol-5-yl)amine (11.0 g, 14.0 mmol) in CH2Cl2 (120 mL) is added dropwise BBr3 (1.0 M CH2Cl2 solution, 18.0 mL, 18.0 mmol) at 0° C. and stirred at room temperature for 10 min. The reaction mixture is quenched by addition of sat. NaHCO3 aq. extracted with ethyl acetate, and the organic layer is washed with brine, dried over magnesium sulfate, filtered and concentrated. The crude product is purified by silica gel column chromatography to give trans-2-(4-{(R)-1-[3-({[3,5-bis(trifluoromethyl)benzyl](2-methyl-2H-tetrazol-5-yl)amino}methyl)-6,7-difluoroquinolin-2-yl]pyrrolidin-2-yl}cyclohexyl)ethanol.

Workup

  1. customThe reaction mixture is quenched by addition of sat. NaHCO3 aq.
  2. extractionextracted with ethyl acetate
  3. washthe organic layer is washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-0cda69cb75a344559ca44eff7c077887
Source dataset
uspto-grants-2013_04
Patent number
US08410275B2

Reaction notes

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