Triethylamine → 4-[1-(4-Methanesulfonyl-phenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy]-piperidine-1-carboxylic acid cyclopentylmethyl ester

HRID 719461

Reaktionsgleichung

Reaktionsgleichung von HRID 719461
N1([C:6](N2C=CN=C2)=[O:7])C=CN=C1.[CH:13]1([CH2:18][OH:19])[CH2:17][CH2:16][CH2:15][CH2:14]1.[CH3:20][S:21]([C:24]1[CH:29]=[CH:28][C:27]([N:30]2[C:34]3=[N:35][CH:36]=[N:37][C:38]([O:39][CH:40]4[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]4)=[C:33]3[CH:32]=[N:31]2)=[CH:26][CH:25]=1)(=[O:23])=[O:22].C(N(CC)CC)C>CS(C)=O>[CH:13]1([CH2:18][O:19][C:6]([N:43]2[CH2:44][CH2:45][CH:40]([O:39][C:38]3[N:37]=[CH:36][N:35]=[C:34]4[N:30]([C:27]5[CH:28]=[CH:29][C:24]([S:21]([CH3:20])(=[O:22])=[O:23])=[CH:25][CH:26]=5)[N:31]=[CH:32][C:33]=34)[CH2:41][CH2:42]2)=[O:7])[CH2:17][CH2:16][CH2:15][CH2:14]1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 77195CyclopentanemethanolHCID 113608021-(4-methanesulfonyl-phenyl)-4-(piperidin-4-yloxy)-1H-pyrazolo[3,4-d]pyrimidine

Produkt 1

HCID 218978094-[1-(4-Methanesulfonyl-phenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy]-piperidine-1-carboxylic acid cyclopentylmethyl esterAusbeute 35,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

Di-imidazol-1-yl-methanone (0.51 mmol, 83 mg), and cyclopentyl-methanol (0.51 mmol, 51 mg) were dissolved in DMSO (1 mL) and stirred for 30 minutes at room temperature. Then, 1-(4-methanesulfonyl-phenyl)-4-(piperidin-4-yloxy)-1H-pyrazolo[3,4-d]pyrimidine (0.17 mmol, 70 mg) and triethylamine (0.51 mmol, 72 μL) were added and heated in a microwave at 120° C. for 6 minutes. The progress of the reaction was monitored by LCMS. The reaction mixture was quenched with water and the product was extracted with ethylacetate. Removal of organic solvents in vacuo and purification by HPLC provided Compound A120 as a white solid (30 mg, 29%). Exact mass calculated for C24H29N5O5S 499.58, found 500.4 (MH+).

Aufarbeitung

  1. temperatureheated in a microwave at 120° C. for 6 minutes
  2. customThe reaction mixture was quenched with water
  3. extractionthe product was extracted with ethylacetate
  4. customRemoval of organic solvents
  5. customin vacuo and purification by HPLC

Quellen und Nachweise

ORD-Eintrag
ord-6587019155d845aa9ed530d010c733c5
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07132426B2

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