Triethylamine → HCID 178503368, compound

HRID 1710729Notes

Reaction equation

HRID 1710729 reaction equation
[F:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]1[N:9]=[C:10]([NH2:21])[C:11]([NH2:20])=[N:12][C:13]=1[C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1.[C:22](N1C=CN=C1)(N1C=CN=C1)=[S:23].[CH2:34](N(CC)CC)C>O1CCCC1>[F:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]1[N:9]=[C:10]2[N:21]=[C:34]([S:23][CH3:22])[NH:20][C:11]2=[N:12][C:13]=1[C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 802641,1'-ThiocarbonyldiimidazoleHCID 16070831HCID 16070831, compound

Product 1

HCID 178503368HCID 178503368, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

A stirred mixture of 5-(3-fluoropyridin-4-yl)-6-pyridin-3-ylpyrazine-2,3-diamine (Example 153, 1.00 g, 3.54 mmol), thiocarbonyldiimidazole (1.28 g, 7.1 mmol) and triethylamine (0.72 g, 7.1 mmol) in tetrahydrofuran (12 mL) was heated to 80° C. in sealed tube. After 24 hours, the mixture was cooled and evaporated in vacuo. The residue was purified by silica gel chromatography eluting with dichloromethane/methanol (95:5) to give the title compound (0.60 g, 53%) as a beige solid.

Workup

  1. temperaturethe mixture was cooled
  2. customevaporated in vacuo
  3. customThe residue was purified by silica gel chromatography
  4. washeluting with dichloromethane/methanol (95:5)

Sources & evidence

ORD record
ord-600d21b14c8f4808a3b2eff63c004b3a
Source dataset
uspto-grants-2010_09
Patent number
US07790728B2

Reaction notes

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