Dimethylformamide → HCID 59396049, compound

HRID 1430577Notes

Reaction equation

HRID 1430577 reaction equation
[N:1]1[N:2]([C:6]2[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=2[C:8]([OH:10])=O)[N:3]=[CH:4][CH:5]=1.[N:15]1(O)[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2N=N1.CN(C)CCCN=C=NCC.C(N(C(C)C)CC)(C)C.CN([CH:48]=[O:49])C>C(OCC)(=O)C>[OH:49][CH2:48][C@H:20]1[CH2:19][N:15]([C:8]([C:7]2[CH:11]=[CH:12][CH:13]=[CH:14][C:6]=2[N:2]2[N:1]=[CH:5][CH:4]=[N:3]2)=[O:10])[C@H:23]([CH3:18])[CH2:22][CH2:21]1

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 213135922-(2H-1,2,3-Triazol-2-yl)benzoic acid

Product 1

HCID 59396049HCID 59396049, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl)methanesulfonic acid-[(3,6R)-6-methylpiperidin-3-yl]methanol (1.2 g, 3.3 mmol), 2-(2H-1,2,3-triazol-2-yl)benzoic acid (0.76 g, 4.0 mmol), 1H-benzotriazol-1-ol (0.71 g, 4.7 mmol) and N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide (0.89 g, 4.7 mmol) in DMF (22 mL) was added N,N-diisopropyl-N-ethylamine (2.3 ml, 13 mmol). The mixture was stirred at ambient temperatures for 16 hours, then diluted with ethyl acetate and washed with brine (2×100 mL). The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel flash chromatography eluting with 0-3% methanol in dichloromethane to provide [(2R,5R)-5-(hydroxymethyl)-2-methylpiperidin-1-yl][2-(2H-1,2,3-triazol-2-yl)phenyl]methanone as a clear oil.

Workup

  1. washwashed with brine (2×100 mL)
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel flash chromatography
  6. washeluting with 0-3% methanol in dichloromethane

Sources & evidence

ORD record
ord-3b958fec90c9467abe2bf8abcf8c6f87
Source dataset
uspto-grants-2015_01
Patent number
US08940898B2

Reaction notes

Loading…