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

HRID 1620043ノート

反応式

HRID 1620043 の反応式
[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]

参加物

9

反応物 5

HCID 25517Ammonium Chloride2 回HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 866838426-(cis-2-(Tert-butoxycarbonylamino)cyclohexylamino)-2-chloro-5-fluoronicotinic acid

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒2 回HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-302cfc7e9a584c98be33a95d3af168fe
出典データセット
uspto-grants-2014_07
特許番号
US08772320B2

反応ノート

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