2-Thiophenecarbonyl chloride → HCID 3272150, compound

HRID 497646Notes

Reaction equation

HRID 497646 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](Cl)=[O:7].[Cl:9][C:10]1[CH:18]=[C:17]2[C:13]([C:14]([NH2:19])=[N:15][NH:16]2)=[CH:12][CH:11]=1>N1C=CC=CC=1>[Cl:9][C:10]1[CH:18]=[C:17]2[C:13]([C:14]([NH:19][C:6]([C:2]3[S:1][CH:5]=[CH:4][CH:3]=3)=[O:7])=[N:15][NH:16]2)=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 789282-Thiophenecarbonyl chlorideHCID 856286-chloro-1H-indazol-3-amine

Product 1

HCID 3272150HCID 3272150, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
6 °C

Procedure

0.64 cm3 of 2-thiophenecarbonyl chloride is added to 1 g of 6-chloro-1H-indazole-3-amine in 15 cm3 of pyridine, after cooling to about 6° C. with an ice bath, the reaction medium is then allowed to return to room temperature over 17 hours and concentrated to dryness under reduced pressure (2 kPa; 45° C.), and the residue is then taken up in 20 cm3 of ethyl acetate, 20 cm3 of water and 20 cm3 of saturated aqueous sodium chloride solution. The organic phase is separated out after settling of the phases has taken place, dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (2 kPa; 45° C.), and the residue is then purified by chromatography under an argon pressure of 50 kPa, on a column of silica gel (particle size 15-40 μm; diameter 3 cm), eluting with a dichloromethane/methanol mixture (99/1 by volume). The fractions containing the expected product are combined and evaporated under reduced pressure (2 kPa; 50° C.); after drying (90 Pa; 50° C.), 660 mg of N-(6-chloro-1H-indazol-3-yl)-2-thiophenecarboxamide are obtained in the form of a pale yellow solid melting at 215° C.

Workup

  1. concentrationconcentrated to dryness under reduced pressure (2 kPa; 45° C.)
  2. customThe organic phase is separated out
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated to dryness under reduced pressure (2 kPa; 45° C.)
  6. customthe residue is then purified by chromatography under an argon pressure of 50 kPa
  7. washon a column of silica gel (particle size 15-40 μm; diameter 3 cm), eluting with a dichloromethane/methanol mixture (99/1 by volume)
  8. additionThe fractions containing the expected product
  9. customevaporated under reduced pressure (2 kPa; 50° C.)
  10. dry with materialafter drying (90 Pa; 50° C.), 660 mg of N-(6-chloro-1H-indazol-3-yl)-2-thiophenecarboxamide

Sources & evidence

ORD record
ord-3c0ed958127f425d83b4db2e8737322d
Source dataset
uspto-grants-2005_09
Patent number
US06949579B2

Reaction notes

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