HCID 58922510, compound → HCID 58922475, compound

HRID 639166Notes

Reaction equation

HRID 639166 reaction equation
C[Si](C)(C)CC[O:5][C:6]([C:8]1[CH:13]([C:14]2[CH:19]=[CH:18][C:17]([C:20]#[N:21])=[CH:16][CH:15]=2)[C:12]([C:22]([NH2:24])=[O:23])=[C:11]([NH2:25])[N:10]([C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:35])([F:34])[F:33])[CH:27]=2)[C:9]=1[CH3:36])=[O:7]>CN(C)C=O.O1CCCC1.O>[NH2:25][C:11]1[N:10]([C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:35])([F:33])[F:34])[CH:27]=2)[C:9]([CH3:36])=[C:8]([C:6]([OH:7])=[O:5])[CH:13]([C:14]2[CH:15]=[CH:16][C:17]([C:20]#[N:21])=[CH:18][CH:19]=2)[C:12]=1[C:22]([NH2:24])=[O:23]

Participants

5

Reactant 1

HCID 58922510HCID 58922510, compound

Product 1

HCID 58922475HCID 58922475, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 650 mg (1.2 mmol) of the compound of Example 59 in 2.4 ml dimethylformamide are added 1.2 ml (1.2 mmol) of a 1 M solution of tris(dimethylamino)sulfoniumdifluoro(trimethyl)silicate in tetrahydrofuran under argon at 0° C. After stirring the reaction mixture for 15 minutes at 0° C., stirring is continued at room temperature overnight. The reaction mixture is diluted with water and extracted four times with ethyl acetate. The combined organic phases are dried with sodium sulfate and concentrated in vacuo. The residue is purified by preparative HPLC (column: YMC C18 ODS-AQ 250 mm×30 mm, 11 μm; solvent A: acetonitrile, solvent B: water; gradient: 0 min 10% A, 3 min 10% A, 11 min 90% A, 13 min 90% A, 13.2 min 10% A, 15 min 10% A; wavelength: 220 nm; injection volume: ca. 1000 μl and 2000 μl methanol solution; number of injections: 2). The product containing fractions are combined and concentrated in vacuo.

Workup

  1. stirringstirring
  2. waitis continued at room temperature overnight
  3. extractionextracted four times with ethyl acetate
  4. dry with materialThe combined organic phases are dried with sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue is purified by preparative HPLC (column: YMC C18 ODS-AQ 250 mm×30 mm, 11 μm; solvent A: acetonitrile, solvent B: water; gradient: 0 min 10% A, 3 min 10% A, 11 min 90% A, 13 min 90% A, 13.2 min 10% A, 15 min 10% A; wavelength: 220 nm; injection volume: ca. 1000 μl and 2000 μl methanol solution; number of injections: 2)
  7. additionThe product containing fractions
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e610421fa6b14b1bbf452c12cd484d33
Source dataset
uspto-grants-2010_04
Patent number
US07691854B2

Reaction notes

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