(1S,2S)-2-phenylcyclopropane-1-carbonyl chloride → (1S,2S)-N-(2-Methyl-7-phenylpyrazolo[1,5-a]pyrimidin-5-yl)-2-phenylcyclopropanecarboxamide

HRID 1409264Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1409264
[C:1]1([C@H:7]2[CH2:9][C@@H:8]2[C:10](Cl)=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:13][C:14]1[CH:29]=[C:17]2[N:18]=[C:19]([NH2:28])[CH:20]=[C:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[N:16]2[N:15]=1>N1C=CC=CC=1>[CH3:13][C:14]1[CH:29]=[C:17]2[N:18]=[C:19]([NH:28][C:10]([C@H:8]3[CH2:9][C@@H:7]3[C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[O:11])[CH:20]=[C:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[N:16]2[N:15]=1

Komponenten

4

Edukt 2

HCID 7005116(1S,2S)-2-phenylcyclopropane-1-carbonyl chlorideHCID 582071812-Methyl-7-phenylpyrazolo[1,5-a]pyrimidin-5-amine

Produkt 1

HCID 67064526(1S,2S)-N-(2-Methyl-7-phenylpyrazolo[1,5-a]pyrimidin-5-yl)-2-phenylcyclopropanecarboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

In a round-bottomed flask was (1S,2S)-2-phenylcyclopropanecarbonyl chloride (161 mg, 0.892 mmol) added in Pyridine (3 mL) to give a yellow suspension. 2-methyl-7-phenylpyrazolo[1,5-a]pyrimidin-5-amine (10A, 100 mg, 0.446 mmol) was added portionwise at 0° C. The temperature was slowly raised to room temperature. The reaction was quenched with saturated sodium bicarbonate and partitioned between ethyl acetate and water. The separated organic layer was dried over Mg2SO4, filtered, and concentrated under reduced pressure (3×100 mL). The reaction mixture was filtered and purified by preparatory HPLC (70-80% MeCN/H2O gradient+0.01% TFA). Received 46 mg (28%) of yellow solid. 1H NMR (DMSO-d6) δ: 11.28 (s, 1H), 7.94-8.06 (m, 2H), 7.90 (s, 1H), 7.52-7.68 (m, 3H), 7.27-7.35 (m, 2H), 7.16-7.26 (m, 3H), 6.33 (s, 1H), 2.42-2.49 (m, 1H), 2.28-2.43 (m, 4H), 1.50-1.57 (m, 1H), 1.44 (ddd, J=8.1, 6.5, 4.0 Hz, 1H); [α]D20=+294° (c=0.6060, MeOH). ESI-MS: m/z 369.0 (M+H)+.

Aufarbeitung

  1. customIn a round-bottomed flask was
  2. customto give a yellow suspension
  3. customThe reaction was quenched with saturated sodium bicarbonate
  4. custompartitioned between ethyl acetate and water
  5. dry with materialThe separated organic layer was dried over Mg2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure (3×100 mL)
  8. filtrationThe reaction mixture was filtered
  9. custompurified by preparatory HPLC (70-80% MeCN/H2O gradient+0.01% TFA)

Quellen und Nachweise

ORD-Eintrag
ord-72d1f65960c1477587d372d1143d4a08
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08921358B2

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