Triethylamine → HCID 57753660, compound

HRID 225546Notes

Reaction equation

HRID 225546 reaction equation
O[CH2:2][C:3]1[C:4]([CH2:13]O)=[N:5][C:6]([C:9]([F:12])([F:11])[F:10])=[CH:7][CH:8]=1.S(Cl)(C)(=O)=O.C(N(CC)CC)C.CCN(C(C)C)C(C)C.[C:36]1([C:42]([C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[NH2:43])[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>ClCCl.CN(C1C=CN=CC=1)C>[F:10][C:9]([F:12])([F:11])[C:6]1[N:5]=[C:4]2[CH2:13][N:43]([C:42]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)([C:50]3[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=3)[C:44]3[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=3)[CH2:2][C:3]2=[CH:8][CH:7]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 138598TritylamineHCID 57753369[6-(Trifluoromethyl)pyridine-2,3-diyl]dimethanol

Product 1

HCID 57753660HCID 57753660, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 7 mmol (3-hydroxymethyl-6-trifluoromethyl-pyridin-2-yl)-methanol in 20 ml dichloromethane was cooled to 0° C. 0.15 mmol 4-(N,N-dimethylamino)-pyridine and 15 mmol of mesyl chloride was added, followed by careful addition of 28 mmol triethyl amine. After stirring for 1 hour at 0° C., the reaction mixture was extracted with dichloromethane, dried and concentrated. The crude mesylate was dissolved in 10 ml N,N-dimethyl formamide, treated with 21 mmol DIPEA and 9 mmol triphenyl methylamine and hold overnight at 60° C. The resulting mixture was concentrated, diluted with water and extracted 3 times with ethyl acetate. The crude compound was purified by chromatography (SiO2; ethyl acetate/n-heptane 1:4) to give the title compound as a viscous yellow oil. Yield: 37%.

Workup

  1. extractionthe reaction mixture was extracted with dichloromethane
  2. customdried
  3. concentrationconcentrated
  4. dissolutionThe crude mesylate was dissolved in 10 ml N,N-dimethyl formamide
  5. waithold overnight at 60° C
  6. concentrationThe resulting mixture was concentrated
  7. additiondiluted with water
  8. extractionextracted 3 times with ethyl acetate
  9. customThe crude compound was purified by chromatography (SiO2; ethyl acetate/n-heptane 1:4)

Sources & evidence

ORD record
ord-31dd0da9d9524dc9b5b765aef99a4536
Source dataset
uspto-grants-2009_07
Patent number
US07557114B2

Reaction notes

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