Acetonitrile → n-[4-(2,4-Dioxo(1,3-dihydroquinazolin-3-yl))phenyl]{[(5-chloro-3-fluoro(2-thienyl))sulfonyl]amino}carboxamide

HRID 562699

반응식

HRID 562699 반응식
[C:1]([NH:5][S:6]([C:9]1[S:10][C:11]([Cl:15])=[CH:12][C:13]=1[F:14])(=[O:8])=[O:7])(C)(C)C.C1CCN2C(=NCCC2)CC1.FC(F)(F)C(O)=[O:30].[NH2:34][C:35]1[CH:40]=[CH:39][C:38]([N:41]2[C:50](=[O:51])[C:49]3[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=3)[NH:43][C:42]2=[O:52])=[CH:37][CH:36]=1.C(#N)C>C(O)(C(F)(F)F)=O>[O:52]=[C:42]1[N:41]([C:38]2[CH:39]=[CH:40][C:35]([NH:34][C:1]([NH:5][S:6]([C:9]3[S:10][C:11]([Cl:15])=[CH:12][C:13]=3[F:14])(=[O:8])=[O:7])=[O:30])=[CH:36][CH:37]=2)[C:50](=[O:51])[C:49]2[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=2)[NH:43]1

참가 물질

6

반응물 4

HCID 6342AcetonitrileHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 220643913-(4-Aminophenyl)-1,3-dihydroquinazoline-2,4-dione trifluoroacetateHCID 22064462(Tert-butyl)[(5-chloro-3-fluoro(2-thienyl))sulfonyl]amine

생성물 1

HCID 22064426n-[4-(2,4-Dioxo(1,3-dihydroquinazolin-3-yl))phenyl]{[(5-chloro-3-fluoro(2-thienyl))sulfonyl]amino}carboxamide수율 34%

시약·촉매·용매 1

HCID 6422Trifluoroacetic acid용매

실험 절차

A 19 mg-sample (0.07 mmol) of (tert-butyl)[(5-chloro-3-fluoro(2-thienyl))sulfonyl]amine was dissolved in neat TFA and stirred for 1 h, concentrated in vacuo and used directly in the next transformation. This sample was dissolved in 150 μL of DCM and 21 mg (0.084 mmol) of DSC was added followed by 21 μL (0.14 mmol) of DBU. This solution was stirred for 18 h, 26 mg (0.07) of 3-(4-aminophenyl)-1,3-dihydroquinazoline-2,4-dione trifluoroacetate salt was added plus 150 μL of dry acetonitrile and refluxed for 2 h. This material was then purified on RP-HPLC to afford 11 mg (34%) of the desired product. ES-MS: M+H+=495 (Cl).

후처리

  1. concentrationconcentrated in vacuo
  2. dissolutionThis sample was dissolved in 150 μL of DCM
  3. addition21 mg (0.084 mmol) of DSC was added
  4. stirringThis solution was stirred for 18 h
  5. temperaturerefluxed for 2 h
  6. customThis material was then purified on RP-HPLC

출처 및 근거

ORD 기록
ord-f98dc765f8c845b9a172887e9eb11a6e
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08067428B2

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