Acetic Acid → HCID 86613791, compound

HRID 2378109Notes

Reaction equation

HRID 2378109 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[CH2:54][CH3:55])=[O:40])([CH3:37])[CH3:36].[Cl-].[NH4+]>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[CH2:54][CH3:55])=[O:40])([CH3:37])[CH3:36]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 25517Ammonium ChlorideHCID 1362473,5-Bis(trifluoromethyl)benzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 86613790HCID 86613790, compound

Product 1

HCID 86613791HCID 86613791, compoundYield 88.1%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

Add sodium triacetoxyborohydride (0.091 mg, 0.409 mmol) to a mixture of 3,5-bis(trifluoromethyl)benzaldehyde (0.045 mL, 0.273 mmol), acetic acid (0.018 mL, 0.303 mmol) and (+/−)-cis-4-amino-2-ethyl-6-methoxy-3,4-dihydro-2H-[1,5]naphthyridine-1-carboxylic acid isopropyl ester (0.08 mg, 0.273 mmol) in dichloroethane (3 mL). Stir the mixture at room temperature under an atmosphere of nitrogen for 14 h. Add a saturated solution of ammonium chloride, separate the layers, and extract the aqueous layer with dichloromethane. 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, to afford the title compound (125 mg, 88%). MS (ES+): 520 (M+H).

Workup

  1. customseparate the layers
  2. extractionextract the aqueous layer with dichloromethane
  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

Sources & evidence

ORD record
ord-e022fb65567448a08c0fe689b34c5e37
Source dataset
uspto-grants-2008_12
Patent number
US07470705B2

Reaction notes

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