Ethylene Glycol → HCID 59218308, compound

HRID 2246394Notes

Reaction equation

HRID 2246394 reaction equation
N1([C:6]([C:8]2[CH:9]([C:26]3[CH:33]=[CH:32][C:29]([C:30]#[N:31])=[CH:28][CH:27]=3)[NH:10][C:11](=[O:25])[N:12]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=3)[C:13]=2[CH3:14])=[O:7])C=CN=C1.[CH2:34]([OH:37])[CH2:35][OH:36]>>[C:30]([C:29]1[CH:28]=[CH:27][C:26]([CH:9]2[C:8]([C:6]([O:36][CH2:35][CH2:34][OH:37])=[O:7])=[C:13]([CH3:14])[N:12]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:22])([F:24])[F:23])[CH:16]=3)[C:11](=[O:25])[NH:10]2)=[CH:33][CH:32]=1)#[N:31]

Participants

3

Reactant 2

HCID 174Ethylene GlycolHCID 58674209HCID 58674209, compound

Product 1

HCID 59218308HCID 59218308, compound

Conditions

Temperature
100 °C

Procedure

45.1 mg (0.1 mmol) of the compound of Example 25 are added to 0.5 ml ethylene glycol. The reaction mixture is stirred at approx. 100° C. for 1 hour. After cooling the reaction mixture is purified by preparative HPLC (column: Agilent Zorbax Extend C18 20 mm×50 mm, 5 μm; solvent A: acetonitrile, solvent B: water+0.1% conc. ammonia; gradient: 0 min 10% A, 2 min 10% A, 6 min 90% A, 7 min 90% A, 7.1 min 10% A, 8 min 10% A; wavelength: 220 nm; injection volume: approx. 500 μl; number of injections: 1). The product containing fractions are combined and concentrated in vacuo.

Workup

  1. temperatureAfter cooling the reaction mixture
  2. customis purified by preparative HPLC (column: Agilent Zorbax Extend C18 20 mm×50 mm, 5 μm; solvent A: acetonitrile, solvent B: water+0.1% conc. ammonia; gradient: 0 min 10% A, 2 min 10% A, 6 min 90% A, 7 min 90% A, 7.1 min 10% A, 8 min 10% A; wavelength: 220 nm; injection volume: approx. 500 μl; number of injections: 1)
  3. additionThe product containing fractions
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-585be5cc9c014ada80a3a6082b1059cb
Source dataset
uspto-grants-2010_03
Patent number
US07687510B2

Reaction notes

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