Triphenylphosphine → HCID 10473450, compound

HRID 488920Notes

Reaction equation

HRID 488920 reaction equation
[CH3:1]C(OC(/N=N/C(OC(C)C)=O)=O)C.[NH2:15][C:16]1[C:24]2[C:19](=[N:20][C:21](N3CCC(NCC(O)C4C=CC(NS(C)(=O)=O)=CC=4)CC3)=[CH:22][C:23]=2[CH2:25]CC)[S:18][C:17]=1[C:49]([NH2:51])=[O:50].[OH:52][C:53]1[CH:61]=[CH:60][C:56]([C:57]([NH2:59])=[O:58])=[CH:55][CH:54]=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]([CH3:1])=[CH:22][C:23]=2[CH2:25][O:52][C:53]2[CH:61]=[CH:60][C:56]([C:57](=[O:58])[NH2:59])=[CH:55][CH:54]=2)[S:18][C:17]=1[C:49]([NH2:51])=[O:50]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 650524-HydroxybenzamideHCID 5363146Diisopropyl azodicarboxylateHCID 23586265HCID 23586265, 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-de4cc91d112c4409844cf3f305125bce
Source dataset
uspto-grants-2005_12
Patent number
US06974870B2

Reaction notes

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