Ammonia → 2-[(3R)-3-fluoro-pyrrolidin-1-yl]-6-methyl-4-morpholin-4-yl-benzamide

HRID 515189Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 515189
[F:1][C@@H:2]1[CH2:6][CH2:5][N:4]([C:7]2[CH:14]=[C:13]([N:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)[CH:12]=[C:11]([CH3:21])[C:8]=2[C:9]#[N:10])[CH2:3]1.N.S(=O)(=O)(O)[OH:24]>>[F:1][C@@H:2]1[CH2:6][CH2:5][N:4]([C:7]2[CH:14]=[C:13]([N:15]3[CH2:16][CH2:17][O:18][CH2:19][CH2:20]3)[CH:12]=[C:11]([CH3:21])[C:8]=2[C:9]([NH2:10])=[O:24])[CH2:3]1

Komponenten

4

Edukt 3

HCID 222AmmoniaHCID 1118Sulfuric AcidHCID 866997552-[(3R)-3-fluoro-pyrrolidin-1-yl]-6-methyl-4-morpholin-4-yl-benzonitrile

Produkt 1

HCID 866997572-[(3R)-3-fluoro-pyrrolidin-1-yl]-6-methyl-4-morpholin-4-yl-benzamideAusbeute 68 %

Versuchsvorschrift

A solution of 2-[(3R)-3-fluoro-pyrrolidin-1-yl]-6-methyl-4-morpholin-4-yl-benzonitrile (0.18 g, 0.62 mmol) in sulphuric acid (8 ml) is heated at 100° C. for 1 h. After completion of the reaction (monitored by TLC), the mixture is poured onto ice water. The aqueous layer is basified with aqueous ammonia to pH 10 and extracted with ethyl acetate (3×20 ml). The combined organic layers are washed with water (10 ml), dried over sodium sulfate and concentrated in vacuo yielding 2-[(3R)-3-fluoro-pyrrolidin-1-yl]-6-methyl-4-morpholin-4-yl-benzamide (0.13 g, 0.423 mmol, 68%).

Aufarbeitung

  1. customAfter completion of the reaction (monitored by TLC)
  2. additionthe mixture is poured onto ice water
  3. extractionextracted with ethyl acetate (3×20 ml)
  4. washThe combined organic layers are washed with water (10 ml)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-2244398160cd4f678c0e7a9ff9942330
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09108936B2

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