Triethylamine → HCID 60026288, compound

HRID 400695Notes

Reaction equation

HRID 400695 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:31][CH3:32])=[C:6]([C:8]([CH3:30])([CH3:29])[CH2:9][C:10]([OH:28])([C:24]([F:27])([F:26])[F:25])[CH2:11][C:12]2[NH:13][C:14]3[CH:15]=[CH:16][CH:17]=[C:18]([C:21]([OH:23])=O)[C:19]=3[CH:20]=2)[CH:7]=1.C([N:35](CC)CC)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[OH-].[NH4+]>C(#N)C.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:31][CH3:32])=[C:6]([C:8]([CH3:29])([CH3:30])[CH2:9][C:10]([OH:28])([C:24]([F:27])([F:25])[F:26])[CH2:11][C:12]2[NH:13][C:14]3[CH:15]=[CH:16][CH:17]=[C:18]([C:21]([NH2:35])=[O:23])[C:19]=3[CH:20]=2)[CH:7]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 14923Ammonium HydroxideHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 60026523HCID 60026523, compound

Product 1

HCID 60026288HCID 60026288, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A solution 2-[4-(5-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-trifluoromethylpentyl]-1H-indole-4-carboxylic acid (170 mg, 0.375 mmol) in 2 mL of acetonitrile was treated with 105 mL of triethylamine and TBTU (133 mg, 0.413 mmol). After 15 minutes, 53.6 mL of ammonium hydroxide solution was added. The resulting reaction mixture was diluted with water and extracted with dichloromethane. The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo. Chromatography on SiO2 (50% ethyl acetate in hexanes) gave 170 mg of the title product as an off-white solid (quantitative yield).

Workup

  1. customThe resulting reaction mixture
  2. extractionextracted with dichloromethane
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1fede97f4ba9449faec57050de0ee06c
Source dataset
uspto-grants-2014_06
Patent number
US08741897B2

Reaction notes

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