Hydrochloric Acid → HCID 59681856, 화합물

HRID 1394108

반응식

HRID 1394108 반응식
[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

참가 물질

8

반응물 5

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 21363Cyclohexaneacetic acidHCID 65578Oxalyl chlorideHCID 87730500HCID 87730500, 화합물

생성물 2

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-3c18c28e22814bbbb6300517dfb6ce91
출처 데이터셋
uspto-grants-2008_03
특허 번호
US07348347B2

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