2-Thiopheneacetyl chloride → HCID 57737169, compound

HRID 1157571Notes

Reaction equation

HRID 1157571 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[C:9]([C:18]3[CH:19]=[C:20]([CH:22]=[CH:23][CH:24]=3)[NH2:21])=[N:10][N:11]3[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[C:12]=23)[CH:5]=[CH:4][N:3]=1.[S:25]1[CH:29]=[CH:28][CH:27]=[C:26]1[CH2:30][C:31](Cl)=[O:32].C([O-])(O)=O.[Na+]>C1COCC1>[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[C:9]([C:18]3[CH:19]=[C:20]([NH:21][C:31](=[O:32])[CH2:30][C:26]4[S:25][CH:29]=[CH:28][CH:27]=4)[CH:22]=[CH:23][CH:24]=3)=[N:10][N:11]3[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[C:12]=23)[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 1623622-Thiopheneacetyl chlorideHCID 516892Sodium BicarbonateHCID 595114323-[3-(2-Chloro-4-pyrimidinyl)-4-fluoropyrazolo[1,5-a]pyridin-2-yl]aniline

Product 1

HCID 57737169HCID 57737169, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the solution of 3-[3-(2-chloro-4-pyrimidinyl)-4-fluoropyrazolo[1,5-a]pyridin-2-yl]aniline (0.28 g) in THF (15 mL) was added 2-thienylacetyl chloride (0.16 g). The reaction was kept stirring at RT for 0.5 h and worked up with sat. NaHCO3 solution (8 mL). After extraction with EtOAc (2×10 mL), drying with Na2SO4, and concentration, the crude mixture was purified through silica gel column chromatography to afford N-{3-[3-(2-chloro-4-pyrimidinyl)-4-fluoropyrazolo[1,5-a]pyridin-2-yl]phenyl}-2-(2-thienyl)acetamide as a yellow solid (0.36 g, 95%). ES-LC/MS m/z=464 [M+H]+.

Workup

  1. extractionAfter extraction with EtOAc (2×10 mL)
  2. dry with materialdrying with Na2SO4, and concentration
  3. customthe crude mixture was purified through silica gel column chromatography

Sources & evidence

ORD record
ord-f9e48320117e4d0eba0db95ca58808a6
Source dataset
uspto-grants-2010_10
Patent number
US07807673B2

Reaction notes

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