Triethylamine → HCID 11649678, Verbindung

HRID 969587Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 969587
OC(C(F)(F)F)=O.[CH:8]([C@:11]1([C:17]([N:19]2[CH2:28][CH2:27][C:26]3[C:21](=[CH:22][C:23]([C:29]([F:32])([F:31])[F:30])=[CH:24][CH:25]=3)[CH2:20]2)=[O:18])[CH2:15][CH2:14][C@@H:13]([NH2:16])[CH2:12]1)([CH3:10])[CH3:9].[OH:33][C:34]1([C:41]2[S:45][C:44]([CH3:46])=[N:43][CH:42]=2)[CH2:39][CH2:38][C:37](=O)[CH2:36][CH2:35]1.C(N(CC)CC)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[CH:8]([C@:11]1([C:17]([N:19]2[CH2:28][CH2:27][C:26]3[C:21](=[CH:22][C:23]([C:29]([F:32])([F:30])[F:31])=[CH:24][CH:25]=3)[CH2:20]2)=[O:18])[CH2:15][CH2:14][C@@H:13]([NH:16][CH:37]2[CH2:36][CH2:35][C:34]([C:41]3[S:45][C:44]([CH3:46])=[N:43][CH:42]=3)([OH:33])[CH2:39][CH2:38]2)[CH2:12]1)([CH3:10])[CH3:9]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 59017431HCID 59017431, VerbindungHCID 86601913HCID 86601913, Verbindung

Produkt 1

HCID 11649678HCID 11649678, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of (1R,3S)-3-isopropyl-3-{[7-(trifluoromethyl)-3,4-dihydroisoquinolin-2(1H)-yl]carbonyl}cyclopentanamine TFA salt (30.0 mg, 0.0846 mmol) from Step C-2 of Example 1 and 4-hydroxy-4-(2-methyl-1,3-thiazol-5-yl)cyclohexanone (25.1 mg, 0.119 mmol) in dichloromethane (8 mL) was added triethylamine (0.0236 mL, 0.169 mmol) followed by sodium triacetoxyborohydride (42 mg, 0.20 mmol) at room temperature. After being stirred overnight, the mixture was quenched by addition of saturated NaHCO3. The resulting solution was extracted with CH2Cl2 three times. The combined extracts were washed with brine, dried over Na2SO4 and concentrated. The residue was purified by flash chromatography on silica gel eluting with 5% MeOH/CH2Cl2 to give two isomers (15 and 12 mg). LC-MS for both isomers: calculated for C29H38F3N3O2S (M+H)+550; found 550.2.

Aufarbeitung

  1. customthe mixture was quenched by addition of saturated NaHCO3
  2. extractionThe resulting solution was extracted with CH2Cl2 three times
  3. washThe combined extracts were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography on silica gel eluting with 5% MeOH/CH2Cl2
  7. customto give two isomers (15 and 12 mg)

Quellen und Nachweise

ORD-Eintrag
ord-f29aedf0d93e44368e86408598623529
Quelldatensatz
uspto-grants-2007_12
Patentnummer
US07307086B2

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