Hydrochloric Acid → [6-(3-Quinolin-4-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-2-yl)-pyridin-2-yl]-methanol

HRID 8274

Reaction equation

HRID 8274 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]2[C:12]([C:19]3[C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[N:22]=[CH:21][CH:20]=3)=[C:13]3[CH2:18][CH2:17][CH2:16][N:14]3[N:15]=2)[N:6]=1)=O.[BH4-].[Li+].Cl>CO>[N:22]1[C:23]2[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:19]([C:12]2[C:11]([C:7]3[N:6]=[C:5]([CH2:3][OH:2])[CH:10]=[CH:9][CH:8]=3)=[N:15][N:14]3[CH2:16][CH2:17][CH2:18][C:13]=23)=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4148881Lithium borohydride2×HCID 66678270Methyl 6-(3-(quinolin-4-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-2-yl)picolinate

Product 1

HCID 10154449[6-(3-Quinolin-4-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-2-yl)-pyridin-2-yl]-methanolYield 58.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 6-(3-quinolin-4-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-2-yl)pyridine-2-carboxylic acid methyl ester (0.550 g, 1.48 mmol) in methanol (20 mL) is added lithium borohydride (35.5 mg, 1.63 mmol). The mixture is stirred 1 h, additional lithium borohydride (35.5 mg, 1.63 mmol) added, and the resulting mixture stirred at room temperature for 16 h. 4 N Hydrochloric acid (3 mL) is added slowly and the resulting mixture concentrated in vacuo. The residue is taken up in methanol (10 mL) and partitioned between ethyl acetate (150 mL) and saturated potassium carbonate (150 mL). The organic portion is washed with brine (150 mL), dried (magnesium sulfate), and a concentrated in vacuo. The residue is precipitated from ethyl acetate with hexanes to yield 296 mg (58%) of the title compound.

Workup

  1. stirringthe resulting mixture stirred at room temperature for 16 h
  2. concentrationthe resulting mixture concentrated in vacuo
  3. custompartitioned between ethyl acetate (150 mL) and saturated potassium carbonate (150 mL)
  4. washThe organic portion is washed with brine (150 mL)
  5. dry with materialdried (magnesium sulfate)
  6. concentrationa concentrated in vacuo
  7. customThe residue is precipitated from ethyl acetate with hexanes

Sources & evidence

ORD record
ord-01768c0751dd480d88612be8046d10c7
Source dataset
uspto-grants-2006_08
Patent number
US07087626B2

Linked notes

Loading…