Water → (4R/S)-(3-chloro-4-hydroxy-7-oxo-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-4-yl)methyl 4-methylbenzenesulfonate

HRID 15126

Reaction equation

HRID 15126 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[CH:6]=[CH:7][C:8](=[O:17])[N:9]3[CH2:13][C:12]([OH:16])([CH2:14][OH:15])[C:11]=1[C:10]=23.C(N(CC)CC)C.[C:25]1([CH3:35])[CH:30]=[CH:29][C:28]([S:31](Cl)(=[O:33])=[O:32])=[CH:27][CH:26]=1.O>ClCCl.O1CCCC1.CN(C)C=O.C([Sn](=O)CCCC)CCC>[CH3:35][C:25]1[CH:30]=[CH:29][C:28]([S:31]([O:15][CH2:14][C:12]2([OH:16])[C:11]3=[C:2]([Cl:1])[CH:3]=[N:4][C:5]4[CH:6]=[CH:7][C:8](=[O:17])[N:9]([C:10]=43)[CH2:13]2)(=[O:33])=[O:32])=[CH:27][CH:26]=1

Participants

7

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 23633411(4R/S)-3-Chloro-4-hydroxy-4-(hydroxymethyl)-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one

Product 1

HCID 131728164(4R/S)-(3-chloro-4-hydroxy-7-oxo-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-4-yl)methyl 4-methylbenzenesulfonateYield 95.2%

Reagents, catalysts & solvents 2

HCID 61221Dibutyltin oxideCatalystHCID 86642945dichloromethane tetrahydrofuran DMFSolvent

Procedure

A suspension of (4R/S)-3-chloro-4-hydroxy-4-(hydroxymethyl)-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one (300 mg, 1.2 mmol) in dichloromethane/tetrahydrofuran/N,N-dimethylformamide (10 ml/10 ml/2 ml) was treated with triethylamine (0.25 ml, 1.8 mmol), para-toluenesulphonyl chloride (220 mg, 1.2 mol) and dibutyltin oxide (15 mg, 0.06 mmol). After 3 hours water was added and the phases separated. The organic phase was washed with saturated aqueous sodium bicarbonate solution then dried and evaporated affording the product (465 mg).

Workup

  1. customthe phases separated
  2. washThe organic phase was washed with saturated aqueous sodium bicarbonate solution
  3. customthen dried
  4. customevaporated

Sources & evidence

ORD record
ord-67728f421e3f4195ad806ed49d11f5d7
Source dataset
uspto-grants-2010_06
Patent number
US07732460B2

Linked notes

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