Triethylamine → HCID 58628194, compound

HRID 2113620Notes

Reaction equation

HRID 2113620 reaction equation
[C:1]([C:5]1[CH:14]=[CH:13][C:12]([NH:15][C:16]2[C:25]3[C:20](=[CH:21][C:22]([C:26]4[C:31]([C:32]([F:35])([F:34])[F:33])=[CH:30][CH:29]=[CH:28][N:27]=4)=[CH:23][CH:24]=3)[N:19]=[CH:18][N:17]=2)=[CH:11][C:6]=1[O:7][CH2:8][CH2:9][OH:10])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.CS(Cl)(=O)=O.[P:48]([O-])([O:58][CH2:59][C:60]1[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1)([O:50][CH2:51][C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1)=[O:49]>ClCCl.C(#N)C.[Ag]=O>[CH2:59]([O:58][P:48](=[O:49])([O:50][CH2:51][C:52]1[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=1)[O:10][CH2:9][CH2:8][O:7][C:6]1[CH:11]=[C:12]([NH:15][C:16]2[C:25]3[C:20](=[CH:21][C:22]([C:26]4[C:31]([C:32]([F:34])([F:35])[F:33])=[CH:30][CH:29]=[CH:28][N:27]=4)=[CH:23][CH:24]=3)[N:19]=[CH:18][N:17]=2)[CH:13]=[CH:14][C:5]=1[C:1]([CH3:4])([CH3:2])[CH3:3])[C:60]1[CH:61]=[CH:62][CH:63]=[CH:64][CH:65]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 4193600DibenzylphosphateHCID 22030405HCID 22030405, compound

Product 1

HCID 58628194HCID 58628194, compound

Reagents, catalysts & solvents 3

HCID 92152Silver(II) oxideCatalystHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

Mix 2-{2-tert-butyl-5-[7-(3-trifluoromethyl-pyridin-2-yl)-quinazolin-4-ylamino]-phenoxy}-ethanol (240 mg, 0.5 mmol) and triethyl amine (60 mg, 0.6 mmol) in dichloromethane 10 ml and add methanesulfonyl chloride (60 mg, 0.5 mmol). Stir the solution at room temperature for 1 hour and evaporate to dryness. Re-dissolve the residue in acetonitrile, add dibenzyl phosphate (278 mg, 1.0 mmol) and silver oxide (231 mg, 1.0 mmol) and heat at 70° C. for 24 hours. Filter the mixture through a plug of Celite and evaporate the filtrate to dryness. Partition the residue between ethyl acetate and sodium bicarbonate solution and extract with further ethyl acetate. Dry the combined extracts (MgSO4) and concentrate under reduced pressure to give the title compound.

Workup

  1. customevaporate to dryness
  2. temperatureheat at 70° C. for 24 hours
  3. filtrationFilter the mixture through a plug of Celite
  4. customevaporate the filtrate to dryness
  5. customPartition the residue between ethyl acetate and sodium bicarbonate solution
  6. extractionextract with further ethyl acetate
  7. dry with materialDry the combined extracts (MgSO4)
  8. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-1d87a7856b754145bb2e4d1d00cec7d8
Source dataset
uspto-grants-2008_10
Patent number
US07432275B2

Reaction notes

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