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

반응식

HRID 15126 반응식
[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

참가 물질

7

반응물 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

생성물 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-methylbenzenesulfonate수율 95.2%

시약·촉매·용매 2

HCID 61221Dibutyltin oxide촉매HCID 86642945dichloromethane tetrahydrofuran DMF용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-67728f421e3f4195ad806ed49d11f5d7
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732460B2

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