Triphenylphosphine → HCID 10473450, compound

HRID 1063113Notes

Reaction equation

HRID 1063113 reaction equation
CC(OC(/N=N/C(OC(C)C)=O)=O)C.[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].O[C:32]1[CH:40]=[CH:39][C:35]([C:36]([NH2:38])=[O:37])=[CH:34][CH:33]=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:32]2[CH:40]=[CH:39][C:35]([C:36](=[O:37])[NH2:38])=[CH:34][CH:33]=2)[S:18][C:17]=1[C:28]([NH2:30])=[O:29]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 650524-HydroxybenzamideHCID 5363146Diisopropyl azodicarboxylateHCID 11579568HCID 11579568, compound

Product 1

HCID 10473450HCID 10473450, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

DIAD (23 mg, 0.116 mmol) was added to a solution of 3-amino-4-hydroxymethyl-6-methyl-thieno[2,3-b]pyridine-2-carboxylic acid amide (see Example 12) (25 mg, 0.105 mmol), 4-hydroxy-benzamide (15 mg, 0.116 mmol), and Ph3P (30 mg, 0.116 mmol) in THF (2.5 mL) at 0° C. The mixture was warmed to room temperature and stirred for 24 h. The reaction mixture was concentrated and triturated with 2:1 EtOAc:MeOH giving the title compound (7 mg, 19%) as an orange solid, m.p. >250° C.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customtriturated with 2:1 EtOAc

Sources & evidence

ORD record
ord-1c766ada2b3b4e069b8be8fe9146e60a
Source dataset
uspto-grants-2005_11
Patent number
US06964956B2

Reaction notes

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