Hydrochloric Acid → HCID 80628076, compound

HRID 715425Notes

Reaction equation

HRID 715425 reaction equation
[CH3:1][C:2]1[C:3]([N:11]2[CH:15]=[CH:14][CH:13]=[N:12]2)=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7](O)=[O:8].C(N1C=CN=C1)(N1C=CN=C1)=O.[BH4-].[Na+].Cl.C(=O)(O)[O-].[Na+]>C1COCC1.O>[CH3:1][C:2]1[CH:10]=[C:6]([CH2:7][OH:8])[CH:5]=[N:4][C:3]=1[N:11]1[CH:15]=[CH:14][CH:13]=[N:12]1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 682631,1'-CarbonyldiimidazoleHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 80631789HCID 80631789, compound

Product 1

HCID 80628076HCID 80628076, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-methyl-6-(1H-pyrazol-1-yl)nicotinic acid (2.20 g, 10.8 mmol, Step-2) in THF (50 mL) is added 1,1′-carbonyldiimidazole (2.63 g, 16.2 mmol). After stirring at rt for 14 hours, the mixture is cooled to 0° C., and a solution of sodium borohydride (2.05 g, 54.1 mmol) in cold water (15 mL) is slowly added. After stirring at 0° C. for 15 min, 2 M hydrochloric acid (25 mL) is added carefully. The resulting mixture is poured onto saturated aqueous sodium bicarbonate solution (200 mL), and the aqueous layer is extracted with EtOAc (200 mL). The separated organic layer is dried over sodium sulfate and concentrated in vacuo. The residue is purified by chromatography on silica gel eluting with n-hexane/EtOAc (4:1-2:1) to give 1.18 g (58% yield) of the title compound as a pale yellow oil.

Workup

  1. temperaturethe mixture is cooled to 0° C.
  2. stirringAfter stirring at 0° C. for 15 min
  3. extractionthe aqueous layer is extracted with EtOAc (200 mL)
  4. dry with materialThe separated organic layer is dried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue is purified by chromatography on silica gel eluting with n-hexane/EtOAc (4:1-2:1)

Sources & evidence

ORD record
ord-46290f2cc696402ba718f8c51c5d2b77
Source dataset
uspto-grants-2015_11
Patent number
US09187475B2

Reaction notes

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