Water → HCID 86305808, compound

HRID 712617Notes

Reaction equation

HRID 712617 reaction equation
C([SiH2][O:6][C:7](C)(C)[C:8]1[CH:9]=[C:10]([C:14]2[CH:15]=[C:16]3[C:21](=[N:22][CH:23]=2)[N:20]([C:24]([NH2:26])=[O:25])[CH2:19][CH2:18][CH2:17]3)[CH:11]=[N:12][CH:13]=1)(C)(C)C.N1C=CC=CC=1.C([O-])(O)=O.[Na+].O>C1COCC1.CCOC(C)=O>[OH:6][CH2:7][C:8]1[CH:9]=[C:10]([C:14]2[CH:15]=[C:16]3[C:21](=[N:22][CH:23]=2)[N:20]([C:24]([NH2:26])=[O:25])[CH2:19][CH2:18][CH2:17]3)[CH:11]=[N:12][CH:13]=1

Participants

7

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 516892Sodium BicarbonateHCID 178455442HCID 178455442, compound

Product 1

HCID 86305808HCID 86305808, compoundYield 91.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

6-[5-(tert-Butyl-dimethyl-silanyloxymethyl)-pyridin-3-yl]-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid amide (40 mg, 0.10 mmol) is dissolved in 2.0 mL of THF and HF pyridine (0.04 mL) is added. The mixture is stirred for 2 hrs and saturated aqueous NaHCO3 solution (5 mL) is added along with water (10 mL) and EtOAc (25 mL). The mixture is stirred for 10 min and the aqueous layer is separated, extracted with EtOAc (2×10 mL). The organic layers are combined and concentrated to give the crude product. Purification by flash column chromatography affords 26 mg of the titled product.

Workup

  1. stirringThe mixture is stirred for 10 min
  2. customthe aqueous layer is separated
  3. extractionextracted with EtOAc (2×10 mL)
  4. concentrationconcentrated
  5. customto give the crude product
  6. customPurification by flash column chromatography

Sources & evidence

ORD record
ord-93153b630329400b80900e593a3e796c
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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