Sodium borohydride → HCID 44434931, compound

HRID 130822Notes

Reaction equation

HRID 130822 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[CH:19]=[CH:18][C:7]([O:8][C:9]2[N:14]=[C:13]([C:15]([NH2:17])=[O:16])[CH:12]=[CH:11][CH:10]=2)=[CH:6][CH:5]=1.[BH4-].[Na+]>CO>[CH2:3]([NH:1][CH2:2][CH2:3][C:4]1[CH:19]=[CH:18][C:7]([O:8][C:9]2[N:14]=[C:13]([C:15]([NH2:17])=[O:16])[CH:12]=[CH:11][CH:10]=2)=[CH:6][CH:5]=1)[C:4]1[CH:19]=[CH:18][CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 59730159HCID 59730159, compound

Product 1

HCID 44434931HCID 44434931, compoundYield 30.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Dissolve 6-[4-(2-aminoethyl)phenoxy]pyridine-2-carboxamide (0.0452 g, 0.176 mmol) in methanol (2.9 mL). Add benzaldehlyde (0.018 mL) and 3 Å molecular sieves. Stir at room temperature overnight. Add NaBH4 (0.0066 g, 0.176 mmol). Stir for additional 6.5 hours before filtering and concentrating. Purify by reverse phase chromatography, eluting with 0-99% 0.1% TFA/acetonitrile and 0.1% TFA/water to give the title compound (9.4 mg, 15.4%): MS ES+ 347.9 (M+H)+; HPLC [YMC-Pack Pro C-18 (150×4.6 mm, S-5 microm), acetonitrile in water containing 0.01% concentrated HCl at 1.0 mL/min, 5-95% over 19 min], tR=7.6 min, 100% purity.

Workup

  1. additionAdd benzaldehlyde (0.018 mL) and 3 Å molecular sieves
  2. stirringStir for additional 6.5 hours
  3. filtrationbefore filtering
  4. concentrationconcentrating
  5. customPurify by reverse phase chromatography
  6. washeluting with 0-99% 0.1% TFA/acetonitrile and 0.1% TFA/water

Sources & evidence

ORD record
ord-278975f743bd4677a5688fdbf749540e
Source dataset
uspto-grants-2008_06
Patent number
US07381719B2

Reaction notes

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