Triethylamine → HCID 86594682, compound

HRID 1916683Notes

Reaction equation

HRID 1916683 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:14]=[CH:15][C:16]([C:19]#[C:20][C:21]3[CH:31]=[CH:30][C:24]([O:25][CH2:26][CH:27]([OH:29])[CH3:28])=[CH:23][CH:22]=3)=[N:17][CH:18]=2)=[CH:9][CH:8]=1.C(N(CC)CC)C.C(OC)(C)(C)C>C1COCC1.O>[CH3:1][S:2]([O:29][CH:27]([CH3:28])[CH2:26][O:25][C:24]1[CH:23]=[CH:22][C:21]([C:20]#[C:19][C:16]2[CH:15]=[CH:14][C:13]([C:10]3[CH:9]=[CH:8][C:7]([Cl:6])=[CH:12][CH:11]=3)=[CH:18][N:17]=2)=[CH:31][CH:30]=1)(=[O:4])=[O:3]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 15413tert-Butyl methyl etherHCID 31297Methanesulfonyl chlorideHCID 67363734HCID 67363734, compound

Product 1

HCID 86594682HCID 86594682, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

0.35 mL (4.50 mmol) methanesulphonic acid chloride are added at RT to a solution of 1.50 g (4.12 mmol) 1-{4-[5-(4-chloro-phenyl)-pyridin-2-ylethynyl]-phenoxy}-propan-2-ol and 1.14 mL (8.20 mmol) triethylamine in 80 mL THF and the reaction is stirred for 3 h at this temperature. The solvent is eliminated i.vac. and the residue is combined with 40 mL tert-butylmethylether and 60 mL water. The precipitate is suction filtered and further purification is carried out by column chromatography on silica gel (EtOAc).

Workup

  1. filtrationfiltered
  2. customfurther purification

Sources & evidence

ORD record
ord-c277cfd00cc141f3bb2e38a631d69717
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

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