Water → HCID 67077477, compound

HRID 1959597Notes

Reaction equation

HRID 1959597 reaction equation
[C:1](Cl)(=[O:5])[CH:2]([CH3:4])[CH3:3].[NH2:7][CH2:8][C:9]1[C:14]([CH2:15][OH:16])=[C:13]([CH3:17])[CH:12]=[CH:11][N:10]=1.O>C(Cl)Cl.C([O-])([O-])=O.[Na+].[Na+]>[OH:16][CH2:15][C:14]1[C:9]([CH2:8][NH:7][C:1](=[O:5])[CH:2]([CH3:4])[CH3:3])=[N:10][CH:11]=[CH:12][C:13]=1[CH3:17]

Participants

6

Reactant 3

HCID 962WaterHCID 62325Isobutyryl chlorideHCID 441910372-(Aminomethyl)-4-methyl-3-pyridinemethanol

Product 1

HCID 67077477HCID 67077477, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent3×HCID 10340Sodium CarbonateSolvent

Conditions

Temperature
0 °C

Procedure

A solution of isobutyryl chloride (29 μL, 0.276 mmol) in DCM (0.20 mL) was added to a vigorously stirred mixture of (2-aminomethyl-4-methyl-pyridin-3-yl)-methanol (30 mg, 0.20 mmol) in DCM (1.0 mL) and aqueous Na2CO3 (1 M, 1 mL) at 0° C. After stirring for 30 min at 0° C., DCM (10 mL) and water (1 mL) was added, and the aqueous layer was extracted with DCM (1×10 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (elution with MeOH/DCM 1:20) to give the title compound. MS (m/z): 223.0 [M+H+].

Workup

  1. extractionthe aqueous layer was extracted with DCM (1×10 mL)
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography on silica gel (elution with MeOH/DCM 1:20)

Sources & evidence

ORD record
ord-bad5aab4e1644cf39c9e731e298f8ee3
Source dataset
uspto-grants-2013_04
Patent number
US08410134B2

Reaction notes

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