Triphenylphosphine → 3-(Aminomethyl)-N-(4-chlorobenzyl)-2-{[[(2R)-2-hydroxy-2-pyridin-2-ylethyl](methyl)amino]methyl}-4-methyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide

HRID 23653Notes

Reaction equation

HRID 23653 reaction equation
[N:1]([CH2:4][C:5]1[C:9]2[N:10]([CH3:26])[CH:11]=[C:12]([C:15]([NH:17][CH2:18][C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=3)=[O:16])[C:13](=[O:14])[C:8]=2[S:7][C:6]=1[CH2:27][N:28]([CH2:30][C@@H:31]([OH:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][N:33]=1)[CH3:29])=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1.O>[NH2:1][CH2:4][C:5]1[C:9]2[N:10]([CH3:26])[CH:11]=[C:12]([C:15]([NH:17][CH2:18][C:19]3[CH:20]=[CH:21][C:22]([Cl:25])=[CH:23][CH:24]=3)=[O:16])[C:13](=[O:14])[C:8]=2[S:7][C:6]=1[CH2:27][N:28]([CH2:30][C@@H:31]([OH:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][N:33]=1)[CH3:29]

Participants

5

Reactant 2

HCID 11776TriphenylphosphineHCID 599852263-(azidomethyl)-N-(4-chlorobenzyl)-2-{[[(2R)-2-hydroxy-2-pyridin-2-ylethyl](methyl)amino]methyl}-4-methyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide

Product 1

HCID 599852193-(Aminomethyl)-N-(4-chlorobenzyl)-2-{[[(2R)-2-hydroxy-2-pyridin-2-ylethyl](methyl)amino]methyl}-4-methyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamideYield 78.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranCatalystHCID 962WaterSolvent

Procedure

A solution of 111 mg of 3-(azidomethyl)-N-(4-chlorobenzyl)-2-{[[(2R)-2-hydroxy-2-pyridin-2-ylethyl](methyl)amino]methyl}-4-methyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide and 58 mg of triphenylphosphine in 2 mL of THF containing 5 drops of water is stirred overnight, then concentrated under reduced pressure with CHCl3/MeOH azeotrope. Flash chromatography on silica gel using 4-10% methanolic ammonia in CH2Cl2 provides 83.1 mg of the amine as a white solid. Recrystallization from acetonitrile furnishes white solid.

Workup

  1. concentrationconcentrated under reduced pressure with CHCl3/MeOH

Sources & evidence

ORD record
ord-784bab6bb17742e8a9275d0917dbc3cb
Source dataset
uspto-grants-2005_02
Patent number
US06852731B2

Reaction notes

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