Potassium Carbonate → tert-Butyl 3-((5-(1-(4-(2,3-dimethylphenoxy)butanoyl)-1,2,3,4-tetrahydroquinolin-5-yl)-2H-tetrazol-2-yl)methyl)phenylcarbamate

HRID 2175267Notes

Reaction equation

HRID 2175267 reaction equation
[NH:1]1[C:5]([C:6]2[CH:15]=[CH:14][CH:13]=[C:12]3[C:7]=2[CH2:8][CH2:9][CH2:10][N:11]3[C:16](=[O:29])[CH2:17][CH2:18][CH2:19][O:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([CH3:27])[C:22]=2[CH3:28])=[N:4][N:3]=[N:2]1.Br[CH2:31][C:32]1[CH:33]=[C:34]([NH:38][C:39](=[O:45])[O:40][C:41]([CH3:44])([CH3:43])[CH3:42])[CH:35]=[CH:36][CH:37]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:28][C:22]1[C:23]([CH3:27])=[CH:24][CH:25]=[CH:26][C:21]=1[O:20][CH2:19][CH2:18][CH2:17][C:16]([N:11]1[C:12]2[C:7](=[C:6]([C:5]3[N:4]=[N:3][N:2]([CH2:31][C:32]4[CH:33]=[C:34]([NH:38][C:39](=[O:45])[O:40][C:41]([CH3:43])([CH3:42])[CH3:44])[CH:35]=[CH:36][CH:37]=4)[N:1]=3)[CH:15]=[CH:14][CH:13]=2)[CH2:8][CH2:9][CH2:10]1)=[O:29]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 14523558tert-Butyl 3-(bromomethyl)phenylcarbamateHCID 178425707HCID 178425707, compound

Product 1

HCID 70982618tert-Butyl 3-((5-(1-(4-(2,3-dimethylphenoxy)butanoyl)-1,2,3,4-tetrahydroquinolin-5-yl)-2H-tetrazol-2-yl)methyl)phenylcarbamateYield 40%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 1-(5-(1H-tetrazol-5-yl)-3,4-dihydroquinolin-1(2H)-yl)-4-(2,3-dimethylphenoxy)butan-1-one (0.16 g, 0.409 mmol), tert-butyl 3-(bromomethyl)phenylcarbamate (0.152 g, 0.531 mmol) and K2CO3 (0.113 g, 0.817 mmol) in DMF (1 mL) was stirred at 80° C. for 16 h. The mixture was partitioned between EtOAc and water. The organic layer was separated, washed with water and brine, dried over anhydrous MgSO4, filtered, and concentrated in vacuo to provide the crude material. The crude material was purified by flash chromatography (0-50% ethyl acetate:hexanes) to afford the title compound (96 mg, 40% yield). LCMS, [M+H]+=597.4.

Workup

  1. customThe mixture was partitioned between EtOAc and water
  2. customThe organic layer was separated
  3. washwashed with water and brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto provide the crude material
  8. customThe crude material was purified by flash chromatography (0-50% ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-609049ff40824eeda5009ecf74df9c87
Source dataset
uspto-grants-2015_06
Patent number
US09062028B2

Reaction notes

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