Hydrazine hydrate (1:1) → (1S,2S,5R)-(2-aminomethyl-7,7-difluoro-3-aza-bicyclo[3.3.0]-oct-3-yl)-(2-methyl-5-m-tolyl-thiazol-4-yl)-methanone

HRID 425807

Reaktionsgleichung

Reaktionsgleichung von HRID 425807
[CH3:1][C:2]1[S:3][C:4]([C:31]2[CH:32]=[C:33]([CH3:37])[CH:34]=[CH:35][CH:36]=2)=[C:5]([C:7]([N:9]2[CH2:16][C@H:15]3[C@H:11]([CH2:12][C:13]([F:18])([F:17])[CH2:14]3)[C@H:10]2[CH2:19][N:20]2C(=O)C3C(=CC=CC=3)C2=O)=[O:8])[N:6]=1.O.NN>CCO>[NH2:20][CH2:19][C@H:10]1[N:9]([C:7]([C:5]2[N:6]=[C:2]([CH3:1])[S:3][C:4]=2[C:31]2[CH:32]=[C:33]([CH3:37])[CH:34]=[CH:35][CH:36]=2)=[O:8])[CH2:16][C@H:15]2[C@@H:11]1[CH2:12][C:13]([F:18])([F:17])[CH2:14]2

Komponenten

4

Edukt 2

HCID 24654Hydrazine hydrate (1:1)HCID 66703707(1S,2S,5R)-2-[3-(2-methyl-5-m-tolyl-thiazole-4-carbonyl)-7,7-difluoro-3-azabicyclo[3.3.0]oct-2-ylmethyl)-isoindole-1,3-dione

Produkt 1

HCID 59411607(1S,2S,5R)-(2-aminomethyl-7,7-difluoro-3-aza-bicyclo[3.3.0]-oct-3-yl)-(2-methyl-5-m-tolyl-thiazol-4-yl)-methanoneAusbeute 92,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of (1S,2S,5R)-2-[3-(2-methyl-5-m-tolyl-thiazole-4-carbonyl)-7,7-difluoro-3-azabicyclo[3.3.0]oct-2-ylmethyl)-isoindole-1,3-dione (130 mg), hydrazine monohydrate (0.078 mL) in EtOH (10 mL) was stirred at reflux for 1 h 45. After cooling to RT, the reaction mixture was concentrated in vacuo, dissolved in DCM, washed twice with water, brine, dried (MgSO4), filtered and concentrated to yield the title compound (90 mg, 92%) as a colorless oil which was used for the next step without further purification. LC-MS: tR=0.79 min; [M+H]+=392

Aufarbeitung

  1. temperatureat reflux for 1 h 45
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. dissolutiondissolved in DCM
  4. washwashed twice with water, brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-7591001438a54518a6eb4305f0d71b60
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08106215B2

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