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Triethylamine → (S)-5-(2,4-difluorophenoxy)-N-(1-(2-hydroxyethyl)-2-oxopiperidin-3-yl)-1-isobutyl-1H-indazole-6-carboxamide

HRID 912460
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 912460
Cl.[NH2:2][C@H:3]1[CH2:8][CH2:7][CH2:6][N:5]([CH2:9][CH2:10][OH:11])[C:4]1=[O:12].C(N(CC)CC)C.O=C1CCC(=O)N1[C:27]1[C:35]2[C:30](=[CH:31][C:32]([C:45]([O-])=[O:46])=[C:33]([O:36][C:37]3[CH:42]=[CH:41][C:40]([F:43])=[CH:39][C:38]=3[F:44])[CH:34]=2)[N:29]([CH2:48][CH:49]([CH3:51])[CH3:50])[N:28]=1>CN(C)C=O.C(OCC)(=O)C>[F:44][C:38]1[CH:39]=[C:40]([F:43])[CH:41]=[CH:42][C:37]=1[O:36][C:33]1[CH:34]=[C:35]2[C:30](=[CH:31][C:32]=1[C:45]([NH:2][C@H:3]1[CH2:8][CH2:7][CH2:6][N:5]([CH2:9][CH2:10][OH:11])[C:4]1=[O:12])=[O:46])[N:29]([CH2:48][CH:49]([CH3:51])[CH3:50])[N:28]=[CH:27]2
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Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 67416461HCID 67416461, VerbindungHCID 866310512,5-dioxopyrrolidin-1-yl-5-(2,4-difluorophenoxy)-1-isobutyl-1H-indazole-6-carboxylate

Produkt 1

HCID 24865100(S)-5-(2,4-difluorophenoxy)-N-(1-(2-hydroxyethyl)-2-oxopiperidin-3-yl)-1-isobutyl-1H-indazole-6-carboxamideAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228
Dimethylformamide
Lösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

(S)-3-Amino-1-(2-hydroxyethyl)piperidin-2-one hydrochloride (52 mg, 0.27 mmol) was dissolved in triethylamine (0.075 mL, 0.54 mmol) and N,N-dimethylformamide (1 mL). To this was added 2,5-dioxopyrrolidin-1-yl-5-(2,4-difluorophenoxy)-1-isobutyl-1H-indazole-6-carboxylate (prepared according to Example 16, Step A; 119 mg, 0.268 mmol), and the reaction mixture was allowed to stir at ambient temperature for 48 hours. The reaction mixture was diluted with ethyl acetate and washed with 1M hydrochloric acid, 1M sodium hydroxide, saturated sodium bicarbonate, and brine. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated. The crude product was purified by flash chromatography on a silica gel column, eluting with 50% acetone/hexanes to yield pure (S)-5-(2,4-difluorophenoxy)-N-(1-(2-hydroxyethyl)-2-oxopiperidin-3-yl)-1-isobutyl-1H-indazole-6-carboxamide (1 h) (104 mg, 80%). Mass spec: 487 (M+1). 1H NMR (CDCl3) δ 8.57 (brd, 1H), 8.32 (s, 1H), 7.87 (s, 1H), 7.14 (m, 1H), 7.03 (s, 1H), 7.00 (m, 1H), 6.89 (m, 1H), 4.47 (ddd, 1H), 4.22 (d, 2H), 3.82 (m, 2H), 3.68 (m, 1H), 3.47 (m, 3H), 2.90 (m, 1H), 2.62 (m, 1H), 2.36 (m, 1H), 2.00 (m, 2H), 1.74 (m, 1H), 0.93 (d, 6H).

Aufarbeitung

  1. washwashed with 1M hydrochloric acid, 1M sodium hydroxide, saturated sodium bicarbonate, and brine
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product was purified by flash chromatography on a silica gel column
  6. washeluting with 50% acetone/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-32c9ada06453464b8dd0c0ccc5f7aff2
Quelldatensatz
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08026233B2

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