4-Hydroxymethylpyridine → HCID 10255724, compound

HRID 2299319Notes

Reaction equation

HRID 2299319 reaction equation
[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11]([OH:26])=[C:12]3[CH:18]=[C:17]([CH2:19][N:20]4[CH2:25][CH2:24][O:23][CH2:22][CH2:21]4)[S:16][C:13]3=[N:14][CH:15]=2)=[O:9])=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N:48]1[CH:53]=[CH:52][C:51]([CH2:54]O)=[CH:50][CH:49]=1.[OH-].[Na+]>C1COCC1>[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11](=[O:26])[C:12]3[CH:18]=[C:17]([CH2:19][N:20]4[CH2:21][CH2:22][O:23][CH2:24][CH2:25]4)[S:16][C:13]=3[N:14]([CH2:54][C:51]3[CH:52]=[CH:53][N:48]=[CH:49][CH:50]=3)[CH:15]=2)=[O:9])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 114724-HydroxymethylpyridineHCID 11776TriphenylphosphineHCID 14798Sodium HydroxideHCID 178522939HCID 178522939, compound

Product 1

HCID 10255724HCID 10255724, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1,4-Diethylazodicarboxylate (205 μL) is added to a solution of N-(4-chlorobenzyl)-4-hydroxy-2-(4-morpholinylmethyl)thieno[2,3-b]pyridine-5-carboxamide (418 mg) from Example No. 41, triphenylphospine (341 mg), and 4-pyridylmethanol (273 mg) in THF (10 mL). The reaction mixture is stirred at room temperature for 20 h and then poured into 0.5 N aqueous NaOH solution (25 mL). The mixture is extracted with EtOAc (3×25 mL). The organic layer is dried (Na2SO4) and concentrated. The crude product is purified by column chromatography (CH2Cl2/methanol, 50/1; 20/1) followed by recrystallization from ethanol to afford 107 mg (21%) of the title compound as a white solid.

Workup

  1. extractionThe mixture is extracted with EtOAc (3×25 mL)
  2. dry with materialThe organic layer is dried (Na2SO4)
  3. concentrationconcentrated
  4. customThe crude product is purified by column chromatography (CH2Cl2/methanol, 50/1; 20/1)
  5. customfollowed by recrystallization from ethanol

Sources & evidence

ORD record
ord-09b9695e58a2495c90037ad23daba0d1
Source dataset
uspto-grants-2002_12
Patent number
US06495683B2

Reaction notes

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