Triethylamine → HCID 71271075, compound

HRID 1525857Notes

Reaction equation

HRID 1525857 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8](O)[C:9]([NH2:11])=[O:10])=[C:4]([F:13])[CH:3]=1.C(N(CC)CC)C.CS(Cl)(=O)=O.Cl.[CH:27]1([N:30]2[CH2:35][C:34]3([CH2:40][CH2:39][NH:38][CH2:37][CH2:36]3)[O:33][CH2:32][C:31]2=[O:41])[CH2:29][CH2:28]1>C(#N)C.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([N:38]2[CH2:39][CH2:40][C:34]3([O:33][CH2:32][C:31](=[O:41])[N:30]([CH:27]4[CH2:28][CH2:29]4)[CH2:35]3)[CH2:36][CH2:37]2)[C:9]([NH2:11])=[O:10])=[C:4]([F:13])[CH:3]=1

Participants

7

Reactant 4

HCID 8471Triethylamine2×HCID 31297Methanesulfonyl chlorideHCID 62225649HCID 62225649, compoundHCID 69083351HCID 69083351, compound

Product 1

HCID 71271075HCID 71271075, compoundYield 55.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-(4-bromo-2-fluorophenyl)-2-hydroxyacetamide (14.35 mmol) and triethylamine (43.1 mmol) in anhydrous acetonitrile (50.0 ml) was added neat methanesulfonyl chloride (20.81 mmol). The reaction stirred at room temperature for 18 hours then additional triethylamine (43.1 mmol) was added followed by solid 4-cyclopropyl-1-oxa-4,9-diazaspiro[5.5]undecan-3-one hydrochloride (15.79 mmol) in one portion. The reaction was heated at 90° C. for 3 hours then cooled to room temperature, diluted with water (150 mL) and stirred for 1 hour. The solids were collected by filtration, rinsed with water, and then dried by air suction and then vacuum to afford the title compound (3.53 g, 55% yield) as a white solid. MS(ES)+ m/e 440.1, 442.3 [M+H]+.

Workup

  1. temperatureThe reaction was heated at 90° C. for 3 hours
  2. temperaturethen cooled to room temperature
  3. stirringstirred for 1 hour
  4. filtrationThe solids were collected by filtration
  5. washrinsed with water
  6. customdried by air suction

Sources & evidence

ORD record
ord-8ddd97f39d4d44ac909806eb9e05c10f
Source dataset
uspto-grants-2015_07
Patent number
US09084794B2

Reaction notes

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