Hydrochloric Acid → [2-Chloro-4-(2,4-difluoro-phenylamino)-phenyl]-{5-[1-(2,3-dihydroxy-propyl)-1H-[1,2,3]triazol-4-yl]-2-methyl-phenyl}-methanone

HRID 2067199Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2067199
[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=2[F:16])[CH:5]=[CH:4][C:3]=1[C:17]([C:19]1[CH:24]=[C:23]([C:25]2[N:26]=[N:27][N:28]([CH2:30][CH:31]3[CH2:35][O:34]C(C)(C)[O:32]3)[CH:29]=2)[CH:22]=[CH:21][C:20]=1[CH3:38])=[O:18].Cl.CCOC(C)=O>C1COCC1>[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=2[F:16])[CH:5]=[CH:4][C:3]=1[C:17]([C:19]1[CH:24]=[C:23]([C:25]2[N:26]=[N:27][N:28]([CH2:30][CH:31]([OH:32])[CH2:35][OH:34])[CH:29]=2)[CH:22]=[CH:21][C:20]=1[CH3:38])=[O:18]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 11497523HCID 11497523, Verbindung

Produkt 1

HCID 11555090[2-Chloro-4-(2,4-difluoro-phenylamino)-phenyl]-{5-[1-(2,3-dihydroxy-propyl)-1H-[1,2,3]triazol-4-yl]-2-methyl-phenyl}-methanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of compound 105 (535 mg, 1.16 mmol) in THF (6.0 mL) was added aqueous HCl (1M, 6 mL)) and the mixture was stirred for 24 h at RT. The reaction mixture was poured into a mixture of EtOAc/saturated NaHCO3. The aqueous phase was washed with more EtOAc. The collected organic phases were washed with water, brine and then dried (MgSO4), filtered and concentrated in vacuo to give the crude product. The crude product was purified by continuous gradient flash chromatography using MeOH/DCM 2:98 to 10:90 as the eluent to afford the title compound as yellow foam. 13C NMR (DMSO-d6) δ 194.9, 158.7 (dd), 155.7 (dd), 149.3, 145.0, 139.8, 135.7, 133.7, 133.7, 131.6, 128.4, 127.1, 126.6, 126.5 (dd), 124.9, 124.2 (dd), 122.3, 114.8, 112.0 (dd), 111.8, 105.0 (dd), 70.3, 63.2, 53.0, 19.4

Aufarbeitung

  1. washThe aqueous phase was washed with more EtOAc
  2. washThe collected organic phases were washed with water, brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give the crude product
  7. customThe crude product was purified by continuous gradient flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-d22df564bb3a4125a4e96e71a6141f52
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08293772B2

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