3-Hydroxybutanal → [2-Chloro-4-(2,4-difluoro-phenylamino)-phenyl]-[5-(3-hydroxy-butylamino)-2-methyl-phenyl]-methanone

HRID 1012634

Reaktionsgleichung

Reaktionsgleichung von HRID 1012634
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:26])=[C:6]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=3[F:24])=[CH:12][C:11]=2[Cl:25])=[O:9])[CH:7]=1.[OH:27][CH:28]([CH3:32])[CH2:29][CH:30]=O>CO>[Cl:25][C:11]1[CH:12]=[C:13]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=2[F:24])[CH:14]=[CH:15][C:10]=1[C:8]([C:6]1[CH:7]=[C:2]([NH:1][CH2:30][CH2:29][CH:28]([OH:27])[CH3:32])[CH:3]=[CH:4][C:5]=1[CH3:26])=[O:9]

Komponenten

4

Edukt 2

HCID 78973-Hydroxybutanal2×HCID 11538012(5-Amino-2-methyl-phenyl)-[2-chloro-4-(2,4-difluoro-phenylamino)-phenyl]-methanone

Produkt 1

HCID 58677686[2-Chloro-4-(2,4-difluoro-phenylamino)-phenyl]-[5-(3-hydroxy-butylamino)-2-methyl-phenyl]-methanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Compound 494 (0.033 g, 0.09 mmol) was suspended in MeOH (1 mL). 3-Hydroxy-butyraldehyde (0.023 g, 0.27 mmol) and NaCN(BH3) (0.055 g, 0.88 mmol) were added. The suspension was stirred at room temperature for 18 h. 3-Hydroxy-butyraldehyde (0.023 g, 0.27 mmol) and NaCN(BH3) (0.055 g, 0.88 mmol) were added again and the suspension was stirred at room temperature for 24 h. The reaction mixture was concentrated in vacuo. The residue was dissolved in EtOAc and the organic phase was washed with brine. The water phase was extracted with EtOAc and the combined organic phases were dried (MgSO4), filtered and concentrated in vacuo. The crude product was purified by flash chromatography using MeOH/CH2Cl2 1:50 as the eluent. This afforded the title compound as oil. 13C NMR (CDCl3) δ 196.7, 159.0 (dd), 155.4 (dd), 147.3, 146.0, 139.6, 135.0, 133.5, 132.0, 129.9, 126.7, 124.6 (dd), 124.0 (dd), 116.3, 115.9, 114.6, 112.8, 111.6 (dd), 104.9 (dd), 67.5, 42.1, 38.0, 24.0, 19.4

Aufarbeitung

  1. stirringthe suspension was stirred at room temperature for 24 h
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. dissolutionThe residue was dissolved in EtOAc
  4. washthe organic phase was washed with brine
  5. extractionThe water phase was extracted with EtOAc
  6. dry with materialthe combined organic phases were dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude product was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-594652d817df48b58b0c2ccaf497811b
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07977387B2

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