3-Pyridinemethanol → HCID 9936087, compound

HRID 1978976Notes

Reaction equation

HRID 1978976 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][CH:51]=[C:50]([CH2:54]O)[CH:49]=1>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:50]3[CH:49]=[N:48][CH:53]=[CH:52][CH:51]=3)[CH:15]=2)=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 75103-PyridinemethanolHCID 11776TriphenylphosphineHCID 178522939HCID 178522939, compound

Product 1

HCID 9936087HCID 9936087, compoundYield 12%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1,4-Diethylazodicarboxylate (205 gL) 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 3-pyridylmethanol (243 μL) in THF (10 mL). The reaction mixture is stirred at room temperature for 20 h and then the resulting suspension is filtered. The crude product is purified by recrystallization from ethanol to afford 63 mg (12%) of the title compound as a white solid.

Workup

  1. filtrationthe resulting suspension is filtered
  2. customThe crude product is purified by recrystallization from ethanol

Sources & evidence

ORD record
ord-9d683be85b1749b4a2442fbdce4c8172
Source dataset
uspto-grants-2001_05
Patent number
US06239142B1

Reaction notes

Loading…