O-(2,4,6-Trimethylbenzenesulfonyl)hydroxylamine → 4-(4-Cyanophenyl)-2,5-dioxo-N-(1-imino-1-oxo-hexahydro-1lambda6-thiopyran-4-yl)-1-(3-(trifluoromethyl)phenyl)-4,5,6,7-tetrahydro-1H-cyclopenta[d]pyrimidine-3(2H)-carboxamide

HRID 927255노트

반응식

HRID 927255 반응식
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[N:14]([C:15]([NH:17][CH:18]3[CH2:23][CH2:22][S:21](=[O:24])[CH2:20][CH2:19]3)=[O:16])[C:13](=[O:25])[N:12]([C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:35])([F:34])[F:33])[CH:27]=3)[C:11]3[CH2:36][CH2:37][C:38](=[O:39])[C:10]2=3)=[CH:5][CH:4]=1)#[N:2].C1(C)C=C(C)C=C(C)C=1S(O[NH2:52])(=O)=O>ClCCl>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[N:14]([C:15]([NH:17][CH:18]3[CH2:23][CH2:22][S:21](=[NH:52])(=[O:24])[CH2:20][CH2:19]3)=[O:16])[C:13](=[O:25])[N:12]([C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:34])([F:35])[F:33])[CH:27]=3)[C:11]3[CH2:36][CH2:37][C:38](=[O:39])[C:10]2=3)=[CH:5][CH:4]=1)#[N:2]

참가 물질

4

반응물 2

HCID 11830845O-(2,4,6-Trimethylbenzenesulfonyl)hydroxylamineHCID 90311366HCID 90311366, 화합물

생성물 1

HCID 903110284-(4-Cyanophenyl)-2,5-dioxo-N-(1-imino-1-oxo-hexahydro-1lambda6-thiopyran-4-yl)-1-(3-(trifluoromethyl)phenyl)-4,5,6,7-tetrahydro-1H-cyclopenta[d]pyrimidine-3(2H)-carboxamide

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

4-(4-Cyanophenyl)-2,5-dioxo-N-(1-oxo-hexahydro-1λ4-thiopyran-4-yl)-1-(3-(trifluoro-methyl)phenyl)-4,5,6,7-tetrahydro-1H-cyclopenta[d]pyrimidine-3(2H)-carboxamide (example 43, 40 mg, 72 μmol) is added to a solution of O-mesitylenesulfonylhydroxyl-amine (66 mg, 0.31 mmol) in dichloromethane (1.0 mL), and the mixture is stirred at room temperature over night. All volatiles are removed under reduced pressure, and the residue is purified by reversed phase HPLC (Waters SunFire™-C18, gradient of acetonitrile in water, 0.1% TFA). Yield: 9 mg; ESI mass spectrum [M+H]+=572; Retention time HPLC: 0.90 min (Z018_S04).

후처리

  1. customAll volatiles are removed under reduced pressure
  2. customthe residue is purified by reversed phase HPLC (Waters SunFire™-C18, gradient of acetonitrile in water, 0.1% TFA)
  3. custom0.90 min (Z018_S04)

출처 및 근거

ORD 기록
ord-76d1ab74255540cab5117b6667c73fa8
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09290459B1

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