Hydrochloric Acid → HCID 59681856、化合物

HRID 1394108

反応式

HRID 1394108 の反応式
[C:1]([Cl:6])(=O)[C:2](Cl)=O.[CH:7]1([CH2:13][C:14]([OH:16])=[O:15])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.Br.[NH2:18][C:19]1[S:20][C:21]2[CH2:27][CH2:26][CH2:25][CH:24]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[C:22]=2[N:23]=1.[ClH:33].[N:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>C(Cl)Cl>[Cl:6][C:1]1[CH:2]=[CH:35][CH:36]=[C:37]([Cl:33])[C:38]=1[CH2:39][N:34]1[CH2:26][CH2:25][CH:24]([CH2:22][NH:23][C:28]([CH:24]2[C:22]3[N:23]=[C:19]([NH:18][C:14](=[O:16])[CH2:13][CH:7]4[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]4)[S:20][C:21]=3[CH2:27][CH2:26][CH2:25]2)=[O:30])[CH2:28]1.[CH:7]1([CH2:13][C:14]([NH:18][C:19]2[S:20][C:21]3[CH2:27][CH2:26][CH2:25][CH:24]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[C:22]=3[N:23]=2)=[O:15])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1

参加物

8

反応物 5

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 21363Cyclohexaneacetic acidHCID 65578Oxalyl chlorideHCID 87730500HCID 87730500、化合物

生成物 2

HCID 59681856HCID 59681856、化合物HCID 866103062-(2-Cyclohexylacetylamino)-4,5,6,7-tetrahydrobenzthiazol-4-carboxylic acid [1-(2,6-dichlorobenzyl)-pyrrolidin-3-yl]methylamide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

Oxalyl chloride (3.10 g, 24.42 mmol) was added to a solution of cyclohexylacetic acid (2.31 g, 16.24 mmol) in DCM (10 mL). The reaction mixture was stirred over a period of two hours at RT under a blanket of nitrogen. The solvent was removed in vacuo, toluene (50 mL) was added and the solvent was again removed. The residue was dissolved in DCM (50 mL) and the resultant solution was slowly added dropwise to a solution of ethyl 2-amino-4,5,6,7-tetrahydrobenzthiazole-4-carboxyate hydrobromide (E) (5.0 g, 16.3 mmol) in pyridine (25 mL) under a blanket of nitrogen. The reaction mixture was stirred for one hour at 0° C. and then overnight at RT. DCM (300 mL) and hydrochloric acid solution (3N in water) were added, the phases were separated, and the aqueous phase was shaken out with DCM (300 mL). The combined organic phases were dried over Na2SO4 and the solvent was removed in vacuo. Following purification by column chromatography (SiO2, EtOAc/heptane 1:2), the residue yielded 4.9 g (86% of theory) of the desired product ethyl 2-(2-cyclohexylacetylamino)-4,5,6,7-tetrahydrobenzthiazol-4-carboxylate (F).

後処理

  1. customThe solvent was removed in vacuo, toluene (50 mL)
  2. additionwas added
  3. customthe solvent was again removed
  4. dissolutionThe residue was dissolved in DCM (50 mL)
  5. stirringThe reaction mixture was stirred for one hour at 0° C.
  6. customovernight
  7. customat RT
  8. customthe phases were separated
  9. stirringthe aqueous phase was shaken out with DCM (300 mL)
  10. dry with materialThe combined organic phases were dried over Na2SO4
  11. customthe solvent was removed in vacuo
  12. custompurification by column chromatography (SiO2, EtOAc/heptane 1:2)

出典と根拠

ORDレコード
ord-3c18c28e22814bbbb6300517dfb6ce91
出典データセット
uspto-grants-2008_03
特許番号
US07348347B2

関連ノート

読み込み中…