Phenol → HCID 11507891, compound

HRID 488919Notes

Reaction equation

HRID 488919 reaction equation
N(C(OC(C)C)=O)=NC(OC(C)C)=O.[NH2:15][C:16]1[C:24]2[C:19](=[N:20][C:21]([CH3:27])=[CH:22][C:23]=2[CH2:25][OH:26])[S:18][C:17]=1[C:28]([NH2:30])=[O:29].[C:31]1(O)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C1COCC1>[NH2:15][C:16]1[C:24]2[C:19](=[N:20][C:21]([CH3:27])=[CH:22][C:23]=2[CH2:25][O:26][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[S:18][C:17]=1[C:28]([NH2:30])=[O:29]

Participants

6

Reactant 4

HCID 996PhenolHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 11579568HCID 11579568, compound

Product 1

HCID 11507891HCID 11507891, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diisopropyl azodicarboxylate (DIAD) (14 mg, 0.069 mmol) was added to a solution of 3-amino-4-hydroxymethyl-6-methyl-thieno[2,3-b]pyridine-2-carboxylic acid amide (15 mg, 0.063 mmol), phenol (6 mg, 0.069 mmol), and Ph3P (18 mg, 0.069 mmol) in THF (1.5 mL) at 0° C. The mixture was warmed to room temperature and stirred for 24 h. The reaction mixture was concentrated and fractionated by preparative TLC (10% MeOH/CH2Cl2) providing the title compound (12 mg, 61%) as an orange solid, m.p. 194-196° C.

Workup

  1. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-9c94a1d9ea764a29ae7b5ddf5c96ff25
Source dataset
uspto-grants-2005_12
Patent number
US06974870B2

Reaction notes

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