Acetic Acid → HCID 86613809, compound

HRID 2378130Notes

Reaction equation

HRID 2378130 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[F:15][C:16]([F:30])([F:29])[C:17]1[CH:18]=[C:19]([CH:22]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:24]=1)[CH:20]=O.C(O)(=O)C.[CH:35]([O:38][C:39]([N:41]1[C:50]2[C:45](=[N:46][C:47]([O:51][CH3:52])=[CH:48][CH:49]=2)[C@H:44]([NH2:53])[CH2:43][C@@H:42]1[CH3:54])=[O:40])([CH3:37])[CH3:36].C(=O)(O)[O-].[Na+]>ClC(Cl)C>[CH:35]([O:38][C:39]([N:41]1[C:50]2[C:45](=[N:46][C:47]([O:51][CH3:52])=[CH:48][CH:49]=2)[C@H:44]([NH:53][CH2:20][C:19]2[CH:18]=[C:17]([C:16]([F:30])([F:29])[F:15])[CH:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:22]=2)[CH2:43][C@@H:42]1[CH3:54])=[O:40])([CH3:37])[CH3:36]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 1362473,5-Bis(trifluoromethyl)benzaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 86613808HCID 86613808, compound

Product 1

HCID 86613809HCID 86613809, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

Add sodium triacetoxyborohydride (1.160 g, 5.50 mmol) to a mixture of 3,5-bis(trifluoromethyl)benzaldehyde (0.217 mL, 1.32 mmol), acetic acid (0.010 mL, 1.65 mmol), and (+/−)-cis-4-amino-6-methoxy-2-methyl-3,4-dihydro-2H-[1,5]naphthyridine-1-carboxylic acid isopropyl ester (0.318 mg, 1.12 mmol) in dichloroethane (10 mL). Stir thie mixture at room temperature under an atmosphere of nitrogen for 14 h. Add a saturated solution of sodium bicarbonate, separate the layers, and extract the aqueous layer with dichioromethane. Dry the combined organic layers over anhydrous sodium sulfate, filter, and remove the solvent under reduced pressure. Purify the residue by flash chromatography, eluting with hexanes/ethyl acetate (gradient eluent, 0-60% ethyl acetate in hexane), to afford the title compound (0.462 g, 83%). MS (ES+): 506 (M+H).

Workup

  1. customseparate the layers
  2. extractionextract the aqueous layer with dichioromethane
  3. dry with materialDry the combined organic layers over anhydrous sodium sulfate
  4. filtrationfilter
  5. customremove the solvent under reduced pressure
  6. customPurify the residue by flash chromatography
  7. washeluting with hexanes/ethyl acetate (gradient eluent, 0-60% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-366f137931d14304ac3fa77dfc987f5c
Source dataset
uspto-grants-2008_12
Patent number
US07470705B2

Reaction notes

Loading…