Acetic Acid → 5-Cyano-furan-2-carboxylic acid (5-hydroxymethyl-2-(4-methyl-piperidin-1-YL)-phenyl)-amide

HRID 33470Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 33470
[CH3:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][OH:15])=[CH:10][C:9]=2[N+:16]([O-])=O)[CH2:4][CH2:3]1.C(O)(=O)C.[H][H].NC1C=C(CO)C=CC=1N1CCC(C)CC1.[C:41]([C:43]1[O:47][C:46]([C:48](Cl)=[O:49])=[CH:45][CH:44]=1)#[N:42].N1CCOCC1>[Pd].C(Cl)Cl.C(OCC)(=O)C.CO>[OH:15][CH2:14][C:11]1[CH:12]=[CH:13][C:8]([N:5]2[CH2:6][CH2:7][CH:2]([CH3:1])[CH2:3][CH2:4]2)=[C:9]([NH:16][C:48]([C:46]2[O:47][C:43]([C:41]#[N:42])=[CH:44][CH:45]=2)=[O:49])[CH:10]=1

Komponenten

11

Edukt 6

HCID 176Acetic AcidHCID 8083MorpholineHCID 202590395-Cyano-2-furoyl chlorideHCID 28963353(4-(4-Methylpiperidin-1-yl)-3-nitrophenyl)methanolHCID 59796772(3-Amino-4-(4-methylpiperidin-1-yl)phenyl)methanolHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 98843185-Cyano-furan-2-carboxylic acid (5-hydroxymethyl-2-(4-methyl-piperidin-1-YL)-phenyl)-amide

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A suspension of 5% Pd/C (5.0 mg, 2.3×10−3 mmol), [4-(4-methyl-piperidin-1-yl)-3-nitro-phenyl]-methanol (i) (95 mg, 0.38 mmol), acetic acid (“HOAc”) (23 mg, 0.38 mmol), methanol (1 mL) and ethyl acetate (4 mL) was stirred in an atmosphere of hydrogen for 3 h. The reaction was filtered, concentrated in vacuo and the resulting [3-amino-4-(4-methyl-piperidin-1-yl)-phenyl]-methanol was used in the next step without further purification. A suspension of [3-amino-4-(4-methyl-piperidin-1-yl)-phenyl]-methanol, 5-cyano-2-furoyl chloride (64 mg, 0.44 mmol), PS morpholine (600 mg, 1.50 mmol), and DCM (10 mL) was stirred at room temperature for 30 min. The reaction was evaporated onto celite, and purified by column chromatography to give 5-cyano-furan-2-carboxylic acid [5-hydroxymethyl-2-(4-methyl-piperidin-1-yl)-phenyl]-amide. MS: 340 (M+1), 1H NMR (CDCl3, 300 MHz): δ 9.9 (s br, 1H), 8.4 (s, 1H), 7.3 (s, 1H), 7.25-7.1 (m, 3H), 4.7 (s, 2H), 3.0 (m, 2H), 2.8 (m, 2H), 1.9, (d, 2H), 1.8-1.4 (m, 3H), 1.1 (d, 3H).

Aufarbeitung

  1. filtrationThe reaction was filtered
  2. concentrationconcentrated in vacuo
  3. customthe resulting [3-amino-4-(4-methyl-piperidin-1-yl)-phenyl]-methanol was used in the next step without further purification
  4. customThe reaction was evaporated onto celite
  5. custompurified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-0fe62a448c1f4b8fa65f1c62f71bbf5b
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07429603B2

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