2-Thiopheneacetyl chloride → N-{3-[3-(2-chloro-4-pyrimidinyl)-6-methylpyrazolo[1,5-a]pyridin-2-yl]phenyl}-2-(2-thienyl)acetamide

HRID 1157649Notes

Reaction equation

HRID 1157649 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[C:9]([C:18]3[CH:19]=[C:20]([NH2:24])[CH:21]=[CH:22][CH:23]=3)=[N:10][N:11]3[CH:16]=[C:15]([CH3:17])[CH:14]=[CH:13][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]>C1COCC1>[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[C:9]([C:18]3[CH:19]=[C:20]([NH:24][C:31](=[O:32])[CH2:30][C:26]4[S:25][CH:29]=[CH:28][CH:27]=4)[CH:21]=[CH:22][CH:23]=3)=[N:10][N:11]3[CH:16]=[C:15]([CH3:17])[CH:14]=[CH:13][C:12]=23)[CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 1623622-Thiopheneacetyl chloride2×HCID 57737218{3-[3-(2-Chloro-4-pyrimidinyl)-6-methylpyrazolo[1,5-a]pyridin-2-yl]phenyl}amine

Product 1

HCID 57737227N-{3-[3-(2-chloro-4-pyrimidinyl)-6-methylpyrazolo[1,5-a]pyridin-2-yl]phenyl}-2-(2-thienyl)acetamideYield 89.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

{3-[3-(2-Chloro-4-pyrimidinyl)-6-methylpyrazolo[1,5-a]pyridin-2-yl]phenyl}amine (0.57 g, 1.68 mmol) and 2-thienylacetyl chloride (0.25 mL, 2.00 mmol) were stirred in THF (30 mL) and stirred for 16 h. Additional 2-thienylacetyl chloride was added until reaction was complete by LC/MS. The mixture was concentrated to dryness and partitioned between aqueous NaHCO3 (saturated) and DCM. The organic layers were concentrated and purified by column chromatography to afford N-{3-[3-(2-chloro-4-pyrimidinyl)-6-methylpyrazolo[1,5-a]pyridin-2-yl]phenyl}-2-(2-thienyl)acetamide as a yellow solid (0.69 g, 89%). ES-LC/MS m/z=460 [M+H]+.

Workup

  1. concentrationThe mixture was concentrated to dryness
  2. custompartitioned between aqueous NaHCO3 (saturated) and DCM
  3. concentrationThe organic layers were concentrated
  4. custompurified by column chromatography

Sources & evidence

ORD record
ord-ecfa4839eb3c4452a2f7958764ab03cc
Source dataset
uspto-grants-2010_10
Patent number
US07807673B2

Reaction notes

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