Dimethylformamide → HCID 57803016, compound

HRID 2102374Notes

Reaction equation

HRID 2102374 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([NH:10][CH3:11])=[O:9])=[N:6][CH:7]=1.[CH2:12](O)[CH2:13][CH2:14][OH:15].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CN(C)C=O.N(C(OC(C)C)=O)=NC(OC(C)C)=O>>[OH:15][CH2:14][CH2:13][CH2:12][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([NH:10][CH3:11])=[O:9])=[N:6][CH:7]=1

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 104421,3-PropanediolHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 231456875-Hydroxy-N-methylpyridine-2-carboxamide

Product 1

HCID 57803016HCID 57803016, compoundYield 80%

Procedure

To a mixture of 5-hydroxy-N-methylpyridine-2-carboxamide (400 mg, 3.0 mmol), 1,3-propanediol (230 mg, 3.0 mmol), triphenylphosphine (786 mg, 3.0 mmol) and N,N-dimethylformamide (4.5 ml, 60 mmol) was added diisopropyl azodicarboxylate (606 mg, 3.0 mmol) while stirring at ambient temperature. After 18 hours, the solvent was removed under reduced pressure and the resulting residue was taken up in ethyl acetate (40 mL) and filtered. The filtrate was concentrated and purified by column chromatography over silica gel using methanol/ethyl acetate (3-4%) to give 488 mg (80%) of 5-(3-hydroxypropoxy)-N-methylpyridine-2-carboxamide as a colorless gum. MS [M+H] 211.2, 1H NMR (CDCl3) δ (ppm) 8.19 (d, J=3.0 Hz, 1H), 8.13 (d, J=8.7 Hz, 1H), 7.83 (b, 1H), 7.28 (m, 1H), 4.21 (t, J=6.3 Hz, 2H), 3.88 (m, 2H), 3.02 (d, J=5.1 Hz), 2.08 (m, 2H).

Workup

  1. customthe solvent was removed under reduced pressure
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated
  4. custompurified by column chromatography over silica gel

Sources & evidence

ORD record
ord-51391491e4334c9fa874f744d0c44bd7
Source dataset
uspto-grants-2009_08
Patent number
US07576080B2

Reaction notes

Loading…