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Hydrochloric Acid → 3-{1-[4-(4-Amino-3-chloro-5-trifluoromethyl-phenyl)-3-hydroxymethyl-butyryl]-piperidin-4-yl}1,3,4,5-tetrahydro-1,3-benzodiazepin-2-one

HRID 1795048
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1795048
[NH2:1][C:2]1[C:33]([C:34]([F:37])([F:36])[F:35])=[CH:32][C:5]([CH2:6][CH:7]([CH2:11][C:12](=[O:31])[N:13]2[CH2:18][CH2:17][CH:16]([N:19]3[CH2:25][CH2:24][C:23]4[CH:26]=[CH:27][CH:28]=[CH:29][C:22]=4[NH:21][C:20]3=[O:30])[CH2:15][CH2:14]2)[C:8](O)=[O:9])=[CH:4][C:3]=1[Cl:38].C1N=CN(C(N2C=NC=C2)=O)C=1.[BH4-].[Na+].Cl>C1COCC1.O>[NH2:1][C:2]1[C:33]([C:34]([F:35])([F:36])[F:37])=[CH:32][C:5]([CH2:6][CH:7]([CH2:8][OH:9])[CH2:11][C:12]([N:13]2[CH2:18][CH2:17][CH:16]([N:19]3[CH2:25][CH2:24][C:23]4[CH:26]=[CH:27][CH:28]=[CH:29][C:22]=4[NH:21][C:20]3=[O:30])[CH2:15][CH2:14]2)=[O:31])=[CH:4][C:3]=1[Cl:38]
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Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 682631,1'-CarbonyldiimidazoleHCID 4311764Sodium borohydrideHCID 221846012-(4-amino-3-chloro-5-trifluoromethyl-benzyl)-4-oxo-4-[4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidin-1-yl]-butyric Acid2×

Produkt 1

HCID 22184595
3-{1-[4-(4-Amino-3-chloro-5-trifluoromethyl-phenyl)-3-hydroxymethyl-butyryl]-piperidin-4-yl}1,3,4,5-tetrahydro-1,3-benzodiazepin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 3.00 g (5.425 mmol) 2-(4-amino-3-chloro-5-trifluoromethyl-benzyl)-4-oxo-4-[4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidin-1-yl]-butyric acid (Intermediate product 68) in 100 mL THF was added 1.054 g (6.500 mmol) CDI and the mixture was stirred for 2 hours at RT. This solution was added dropwise under a nitrogen atmosphere over 5 minutes to an ice-cooled solution of 0.728 g (19.250 mmol) sodium borohydride in 50 mL water and the mixture was stirred for 16 hours at RT. The reaction mixture was acid ified with 1 N aqueous HCl to pH 2 and exhaustively extracted with EtOAc. The combined org. phases were washed with sat. aqueous NaCl solution, dried over sodium sulphate and evaporated i. vac.

Aufarbeitung

  1. stirringthe mixture was stirred for 16 hours at RT
  2. extractionexhaustively extracted with EtOAc
  3. washphases were washed with sat. aqueous NaCl solution
  4. dry with materialdried over sodium sulphate
  5. customevaporated i

Quellen und Nachweise

ORD-Eintrag
ord-5ce44fe6c952441a86bf08d20bf6c8cd
Quelldatensatz
uspto-grants-2006_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07026312B2

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