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

HRID 1157649

Reaktionsgleichung

Reaktionsgleichung von HRID 1157649
[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

Komponenten

4

Edukt 2

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

Produkt 1

HCID 57737227N-{3-[3-(2-chloro-4-pyrimidinyl)-6-methylpyrazolo[1,5-a]pyridin-2-yl]phenyl}-2-(2-thienyl)acetamideAusbeute 89,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

{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]+.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-ecfa4839eb3c4452a2f7958764ab03cc
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07807673B2

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