Ammonium Chloride → Tert-butyl cis-2-(5-aminocarbonyl-6-chloro-3-fluoropyridin-2-ylamino)cyclohexylcarbamate

HRID 2406691노트

반응식

HRID 2406691 반응식
[Cl-].[NH4+].CC[N:5]=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.C(N(C(C)C)CC)(C)C.[C:34]([O:38][C:39]([NH:41][C@H:42]1[CH2:47][CH2:46][CH2:45][CH2:44][C@H:43]1[NH:48][C:49]1[C:57]([F:58])=[CH:56][C:52]([C:53](O)=[O:54])=[C:51]([Cl:59])[N:50]=1)=[O:40])([CH3:37])([CH3:36])[CH3:35]>C(OCC)(=O)C.O.CN(C=O)C>[NH2:5][C:53]([C:52]1[CH:56]=[C:57]([F:58])[C:49]([NH:48][C@H:43]2[CH2:44][CH2:45][CH2:46][CH2:47][C@H:42]2[NH:41][C:39](=[O:40])[O:38][C:34]([CH3:35])([CH3:36])[CH3:37])=[N:50][C:51]=1[Cl:59])=[O:54]

참가 물질

9

반응물 5

HCID 25517Ammonium Chloride2회HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 866838426-(cis-2-(Tert-butoxycarbonylamino)cyclohexylamino)-2-chloro-5-fluoronicotinic acid

생성물 1

HCID 86683847Tert-butyl cis-2-(5-aminocarbonyl-6-chloro-3-fluoropyridin-2-ylamino)cyclohexylcarbamate수율 87.7%

시약·촉매·용매 3

HCID 962Water용매2회HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

Ammonium chloride (1.10 g), WSC.HCl (2.97 g), HOBt.H2O (2.37 g), and diisopropylethylamine (7.06 ml) were added to a DMF solution (40 ml) containing 6-(cis-2-(tert-butoxycarbonylamino)cyclohexylamino)-2-chloro-5-fluoronicotinic acid (2.00 g), followed by stirring at room temperature for 7 hours. A saturated aqueous ammonium chloride solution, water, and ethyl acetate were added to the reaction mixture. The organic layer was collected, washed with saturated saline, and dried over anhydrous magnesium sulfate, and the solvent was distilled away under reduced pressure. Diisopropylether was added to the obtained residue, solid matter was collected by filtration, and a white solid of tert-butyl cis-2-(5-aminocarbonyl-6-chloro-3-fluoropyridin-2-ylamino)cyclohexylcarbamate (1.75 g) was thus obtained.

후처리

  1. customThe organic layer was collected
  2. washwashed with saturated saline
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled away under reduced pressure
  5. additionDiisopropylether was added to the obtained residue, solid matter
  6. filtrationwas collected by filtration

출처 및 근거

ORD 기록
ord-413a053bc9c34832b9d686bf42e55bf7
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08809371B2

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