Hydrochloric Acid → 1-(4-Cyano-7-[(3s)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-6-phenyl-1,3-benzoxazol-2-yl)piperidine-4-carboxylic acid

HRID 17430노트

반응식

HRID 17430 반응식
[C:1]([C:3]1[C:8]2[N:9]=[C:10]([N:12]3[CH2:17][CH2:16][CH:15]([C:18]([O:20]CC)=[O:19])[CH2:14][CH2:13]3)[O:11][C:7]=2[C:6]([N:23]2[CH2:27][CH2:26][C@H:25]([N:28]([CH3:30])[CH3:29])[CH2:24]2)=[C:5]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:4]=1[CH3:37])#[N:2].[OH-].[Na+].Cl>O1CCCC1>[C:1]([C:3]1[C:8]2[N:9]=[C:10]([N:12]3[CH2:17][CH2:16][CH:15]([C:18]([OH:20])=[O:19])[CH2:14][CH2:13]3)[O:11][C:7]=2[C:6]([N:23]2[CH2:27][CH2:26][C@H:25]([N:28]([CH3:30])[CH3:29])[CH2:24]2)=[C:5]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:4]=1[CH3:37])#[N:2]

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2회HCID 68584931Ethyl 1-{4-cyano-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-6-phenyl-1,3-benzoxazol-2-yl}piperidine-4-carboxylate

생성물 1

HCID 685863861-(4-Cyano-7-[(3s)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-6-phenyl-1,3-benzoxazol-2-yl)piperidine-4-carboxylic acid수율 73.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Ethyl 1-{4-cyano-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-6-phenyl-1,3-benzoxazol-2-yl}piperidine-4-carboxylate (I-162) (0.26 g, 0.52 mmol) was dissolved in tetrahydrofuran (10 ml), then 1 N sodium hydroxide (0.60 ml, 0.60 mmol) was added. After stirring at room temperature for 19 hours, 1 N sodium hydroxide (0.40 ml, 0.40 mmol) was further added, followed by stirring at room temperature for 24 hours. 1 N Hydrochloric acid (1.00 ml, 1.00 mmol) was added, then the solvent was evaporated away under reduced pressure. The resulting residue was purified by silica gel column chromatography (chloroform:methanol:water=8:3:0.5), then ethanol and a small amount of ether were added, and the insoluble matter was collected by filtration to obtain a colorless solid (0.18 g, 71%).

후처리

  1. stirringby stirring at room temperature for 24 hours
  2. customthe solvent was evaporated away under reduced pressure
  3. customThe resulting residue was purified by silica gel column chromatography (chloroform:methanol:water=8:3:0.5)
  4. additionethanol and a small amount of ether were added
  5. filtrationthe insoluble matter was collected by filtration

출처 및 근거

ORD 기록
ord-517dcedeb4734de6a7071bc5b7709581
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737166B2

반응 노트

불러오는 중…