3-Thiophenamine, tetrahydro-N,3-dimethyl-, 1,1-dioxide → HCID 59606078, 화합물

HRID 1945666노트

반응식

HRID 1945666 반응식
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[C:7]([CH2:12][CH:13]=O)[N:8]2[CH3:11])=[C:4]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[N:3]=1.[CH3:21][NH:22][C:23]1([CH3:30])[CH2:27][CH2:26][S:25](=[O:29])(=[O:28])[CH2:24]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[C:7]([CH2:12][CH2:13][N:22]([CH3:21])[C:23]3([CH3:30])[CH2:27][CH2:26][S:25](=[O:29])(=[O:28])[CH2:24]3)[N:8]2[CH3:11])=[C:4]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[N:3]=1

참가 물질

5

반응물 3

HCID 31130173-Thiophenamine, tetrahydro-N,3-dimethyl-, 1,1-dioxideHCID 5049666Sodium triacetoxyborohydrideHCID 59605819(2-chloro-9-methyl-6-morpholin-4-yl-9H-purin-8-yl)acetaldehyde

생성물 1

HCID 59606078HCID 59606078, 화합물수율 28%

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

실험 절차

A mixture of (2-chloro-9-methyl-6-morpholin-4-yl-9H-purin-8-yl)acetaldehyde (210 mg, 0.71 mmol), methyl-(3-methyl-1,1-dioxotetrahydrothiophen-3-yl)amine (116 mg, 0.71 mmol), sodium triacetoxyborohydride (301 mg, 1.42 mmol) and 4 Å powdered molecular sieves (280 mg) in DCE (15 mL) was stirred for 23 h. The reaction mixture was filtered through Celite® and the filtrate loaded onto an Isolute® SCX-2 cartridge which was washed with MeOH and the product eluted with 2M NH3/MeOH/DCM. The resulting residue was purified by column chromatography (Si—PCC, MeOH:EtOAc, 0-10%) affording the title compound as a pale yellow solid (87 mg, 28%). LCMS (method H): RT 2.01 min [M+H]+ 443.2

후처리

  1. filtrationThe reaction mixture was filtered through Celite®
  2. washwas washed with MeOH
  3. washthe product eluted with 2M NH3/MeOH/DCM
  4. customThe resulting residue was purified by column chromatography (Si—PCC, MeOH:EtOAc, 0-10%)

출처 및 근거

ORD 기록
ord-a9fbb3d7fb2949daa0dcf363c8c8d284
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08394796B2

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