5-Methylthiophene-2-carboxylic acid → HCID 25225990, compound

HRID 2279660Notes

Reaction equation

HRID 2279660 reaction equation
[C:1]12([CH2:11][NH2:12])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[CH3:13][C:14]1[S:18][C:17]([C:19](O)=[O:20])=[CH:16][CH:15]=1.[Cl-].ClC1N(C)CC[NH+]1C>[OH-].[Na+]>[C:1]12([CH2:11][NH:12][C:19]([C:17]3[S:18][C:14]([CH3:13])=[CH:15][CH:16]=3)=[O:20])[CH2:8][CH:7]3[CH2:6][CH:5]([CH2:4][CH:3]([CH2:9]3)[CH2:2]1)[CH2:10]2

Participants

5

Reactant 3

HCID 747135-Methylthiophene-2-carboxylic acidHCID 86625Tricyclo(3.3.1.13,7)dec-1-ylmethylamineHCID 109867151H-Imidazolium, 2-chloro-4,5-dihydro-1,3-dimethyl-, chloride

Product 1

HCID 25225990HCID 25225990, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
50 °C

Procedure

To a 2 mL reaction vial is added adamantylmethylamine (0.15 mL, 0.2M in toluene), 5-methylthiophene-2-carboxylic acid (0.15 mL, 0.2M in dimethylacetamide), 2-chloro-1,3-dimethylimidazolinium chloride (0.20 mL, 0.2M in ACN), and TEA (0.20 mL, 0.2M in toluene). The mixture is placed on a shaker and heated to 50° C. for 16 h. The mixture is cooled to RT and diluted with 1M aqueous sodium hydroxide (0.5 mL). The resulting mixture is extracted with 50% EtOAc-hexane (3×0.5 mL) and purified over benzenesulfonic acid ion exchange resin (eluted with 50% EtOAc-hexane) to afford the title compound. LC/MS: (M+1)=290.19; RT=1.33 min.

Workup

  1. customTo a 2 mL reaction
  2. temperatureThe mixture is cooled to RT
  3. extractionThe resulting mixture is extracted with 50% EtOAc-hexane (3×0.5 mL)
  4. custompurified over benzenesulfonic acid ion exchange resin (eluted with 50% EtOAc-hexane)

Sources & evidence

ORD record
ord-7fc4566b1b8945d3943ffbb4bc859ce6
Source dataset
uspto-grants-2015_09
Patent number
US09133204B2

Reaction notes

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