Hydrogen Bromide → HCID 178527280, compound

HRID 1711418Notes

Reaction equation

HRID 1711418 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][CH:14]([CH2:17][O:18][C:19]2[CH:20]=[C:21]3[C:25](=[CH:26][CH:27]=2)[NH:24][N:23]=[C:22]3[S:28]([C:31]2[C:40]3[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=3)[CH:34]=[CH:33][CH:32]=2)(=[O:30])=[O:29])[CH2:13][CH2:12]1)=O)C1C=CC=CC=1.Br>C(O)(=O)C.C(OCC)C>[C:31]1([S:28]([C:22]2[C:21]3[C:25](=[CH:26][CH:27]=[C:19]([O:18][CH2:17][CH:14]4[CH2:15][CH2:16][NH:11][CH2:12][CH2:13]4)[CH:20]=3)[NH:24][N:23]=2)(=[O:29])=[O:30])[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:34]=[CH:33][CH:32]=1

Participants

5

Reactant 2

HCID 260Hydrogen BromideHCID 178525139HCID 178525139, compound

Product 1

HCID 178527280HCID 178527280, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 4-[3-(1-naphthylsulfonyl)-1H-indazol-5-yloxymethyl]-piperidine-1-carboxylic acid benzyl ester (0.3 g, 0.54 mmoles) and 33 wt % HBr in acetic acid (1.5 mL) was stirred at room temperature for 30 minutes, diluted with ethyl ether and filtered. The filtercake was washed with ether, dried, treated with 1N NaOH and saturated NaCl and extracted with EtOAc. The extracts were combined, dried over Na2SO4 and concentrated under vacuum to afford the title compound as an off-white solid; mp 175-177° C., identified by HNMR and mass spectral analyses, MS (ES) m/z 420.2.

Workup

  1. filtrationfiltered
  2. washThe filtercake was washed with ether
  3. customdried
  4. additiontreated with 1N NaOH and saturated NaCl
  5. extractionextracted with EtOAc
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-f11689a3f17d43cab865a88350ba6a93
Source dataset
uspto-grants-2010_09
Patent number
US07790751B2

Reaction notes

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