Piconol → HCID 58505427, compound

HRID 475444Notes

Reaction equation

HRID 475444 reaction equation
[CH:1]1([C@H:7]([NH:12][C:13]([C:15]2[O:16][C:17]([C:20]3[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][N:21]=3)=[CH:18][CH:19]=2)=[O:14])[C:8](=[O:11])[NH:9][CH3:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[N:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1CO.[CH:35]1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[CH:1]1([C@H:7]([NH:12][C:13]([C:15]2[O:16][C:17]([C:20]3[CH:25]=[CH:24][C:23]([O:26][CH2:35][C:31]4[CH:32]=[N:27][CH:28]=[CH:29][CH:30]=4)=[CH:22][N:21]=3)=[CH:18][CH:19]=2)=[O:14])[C:8](=[O:11])[NH:9][CH3:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 11474PiconolHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 58505366HCID 58505366, compound

Product 1

HCID 58505427HCID 58505427, compoundYield 34.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 5-(5-hydroxy-pyridin-2-yl)-furan-2-carboxylic acid ((S)-cyclohexyl-methylcarbamoyl-methyl)-amide (170 mg, 0.47 mmol.), 2-pyridine methanol (103 mg, 0.95 mmol) and PPh3 (supported on polystyrene resin, 320 mg 0.95 mmol) in THF (2 mL) is added DIAD (0.18 mL, 0.95 mmol) dropwise at 0° C. under argon. The mixture is allowed to warm to room temperature, stirred for 19 hours, diluted with THF, and filtered through celite. The filtrate is evaporated in vacuo, and the crude material is purified on reverse phase HPLC to yield a white solid 72 mg, 34%, LC/MS ESI m/z (M+H)+=449.7.

Workup

  1. filtrationfiltered through celite
  2. customThe filtrate is evaporated in vacuo
  3. customthe crude material is purified on reverse phase HPLC

Sources & evidence

ORD record
ord-3597152752b449f89f4f7b67db56fd9c
Source dataset
uspto-grants-2014_01
Patent number
US08637550B2

Reaction notes

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