Trifluoroacetic acid → 4-(5-Cyano-7-isopropyl-1,3-benzoxazol-2-yl)-N-(pyrrolidin-3-ylmethyl)benzamide

HRID 2066833Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2066833
[C:1]([C:3]1[CH:4]=[C:5]([CH:34]([CH3:36])[CH3:35])[C:6]2[O:10][C:9]([C:11]3[CH:32]=[CH:31][C:14]([C:15]([NH:17][CH2:18][CH:19]4[CH2:23][CH2:22][N:21](C(OC(C)(C)C)=O)[CH2:20]4)=[O:16])=[CH:13][CH:12]=3)=[N:8][C:7]=2[CH:33]=1)#[N:2].FC(F)(F)C(O)=O>ClCCl>[C:1]([C:3]1[CH:4]=[C:5]([CH:34]([CH3:36])[CH3:35])[C:6]2[O:10][C:9]([C:11]3[CH:12]=[CH:13][C:14]([C:15]([NH:17][CH2:18][CH:19]4[CH2:23][CH2:22][NH:21][CH2:20]4)=[O:16])=[CH:31][CH:32]=3)=[N:8][C:7]=2[CH:33]=1)#[N:2]

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 68409608tert-Butyl 3-({[4-(5-cyano-7-isopropyl-1,3-benzoxazol-2-yl)benzoyl]amino}methyl)pyrrolidine-1-carboxylate

Produkt 1

HCID 684078314-(5-Cyano-7-isopropyl-1,3-benzoxazol-2-yl)-N-(pyrrolidin-3-ylmethyl)benzamideAusbeute 90,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of tert-butyl 3-({[4-(5-cyano-7-isopropyl-1,3-benzoxazol-2-yl)benzoyl]amino}methyl)pyrrolidine-1-carboxylate (910 mg) in dichloromethane (75 ml) was added 20 ml of trifluoroacetic acid. The mixture was stirred at room temperature for 2 h, and then concentrated in vacuo. The residue was basified by the addition of 75 ml of saturated aqueous sodium bicarbonate and diluted with 75 ml of ethyl acetate. The solids were filtered from both layers and dried in vacuo to provide the title compound (655 mg, 90%). Mass spectrum (ESI) 389.9 (M+1).

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. additionThe residue was basified by the addition of 75 ml of saturated aqueous sodium bicarbonate
  3. additiondiluted with 75 ml of ethyl acetate
  4. filtrationThe solids were filtered from both layers
  5. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-8d395143746b4045b5c7d3abdcf8823f
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08293721B2

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