Dimethylformamide → HCID 67265258, compound

HRID 1685150Notes

Reaction equation

HRID 1685150 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[N:15]([CH2:27]COS(C)(=O)=O)[CH:16]=[C:17]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[C:21]([F:26])[CH:20]=3)[N:18]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:34][NH:35][CH2:36][CH2:37][OH:38].[CH3:39]N(C=O)C>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[N:15]([CH2:27][CH2:34][N:35]([CH2:36][CH2:37][OH:38])[CH3:39])[CH:16]=[C:17]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[C:21]([F:26])[CH:20]=3)[N:18]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 80162-(Methylamino)ethanolHCID 86641600HCID 86641600, compound

Product 1

HCID 67265258HCID 67265258, compoundYield 52.2%

Procedure

Combine 4-[4-(3,4-difluoro-phenyl)-1-(2-methanesulfonyloxy-ethyl)-1H-imidazol-2-yl]-piperidine-1-carboxylic acid tert-butyl ester (3.0 g; 0.0061 mol; 1.0 equiv), 2-methylamino-ethanol (1.48 g; 0.031 mol; 5.0 equiv) in DMF (30 mL) and stir at 40-50° C. for 16 h. Quench with water and extract with diethyl ether. Evaporate the organic layer, purify over 50 g silica gel with 0 to 10% MeOH/DCM. Pool fractions to produce the title compound (1.5 g; 52.2%) MS (ES+): m/z=465 (M+H).

Workup

  1. customQuench with water
  2. extractionextract with diethyl ether
  3. customEvaporate the organic layer
  4. custompurify over 50 g silica gel with 0 to 10% MeOH/DCM

Sources & evidence

ORD record
ord-dff998109ccc4cdb82e282f54c2e4acd
Source dataset
uspto-grants-2012_04
Patent number
US08148387B2

Reaction notes

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