Water → HCID 178432379, compound

HRID 1710718Notes

Reaction equation

HRID 1710718 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[C:10]([NH2:21])[C:11]([NH2:20])=[N:12][C:13]=2[C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)[CH:5]=[CH:6][CH:7]=1.O.[C:23](OC(=O)C)(=O)[CH3:24]>>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[C:10]3[NH:21][C:23]([CH3:24])=[N:20][C:11]3=[N:12][C:13]=2[C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 16070570HCID 16070570, compound

Product 1

HCID 178432379HCID 178432379, compoundYield 52%

Conditions

Temperature
140 °C

Procedure

A mixture of 5-(3-fluorophenyl)-6-pyridin-4-ylpyrazine-2,3-diamine (Example 72, 300 mg, 1.07 mmol) in acetic anhydride (3 mL) was stirred and heated at 140° C. for 4 h. Then polyphosphoric acid was added (0.32 g) and allowed to react at the same temperature for 2 h. Upon cooling, water was added and the product extracted with ethyl acetate. The crude obtained was purified by silica column chromatography eluting with a gradient from CH2Cl2 to CH2Cl2/MeOH 95:5 to afford the title compound as a yellow solid (36 mg, 52%).

Workup

  1. customto react at the same temperature for 2 h
  2. temperatureUpon cooling
  3. extractionthe product extracted with ethyl acetate
  4. customThe crude obtained
  5. customwas purified by silica column chromatography
  6. washeluting with a gradient from CH2Cl2 to CH2Cl2/MeOH 95:5

Sources & evidence

ORD record
ord-82881be2e1044edf89a96c907e4e1578
Source dataset
uspto-grants-2010_09
Patent number
US07790728B2

Reaction notes

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