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1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → tert-butyl 3-(3-((3-(3,4-dihydroisoquinolin-2(1H)-yl)-2-hydroxypropyl) carbamoyl)phenyl)pyrrolidine-1-carboxylate

HRID 880290
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HRID 880290 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([C:13]2[CH:14]=[C:15]([CH:19]=[CH:20][CH:21]=2)[C:16]([OH:18])=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[NH2:43][CH2:44][CH:45]([OH:57])[CH2:46][N:47]1[CH2:56][CH2:55][C:54]2[C:49](=[CH:50][CH:51]=[CH:52][CH:53]=2)[CH2:48]1>CN(C=O)C.O>[CH2:48]1[C:49]2[C:54](=[CH:53][CH:52]=[CH:51][CH:50]=2)[CH2:55][CH2:56][N:47]1[CH2:46][CH:45]([OH:57])[CH2:44][NH:43][C:16]([C:15]1[CH:14]=[C:13]([CH:10]2[CH2:11][CH2:12][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:9]2)[CH:21]=[CH:20][CH:19]=1)=[O:18]
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참가 물질

7

반응물 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 167907201-amino-3-(3,4-dihydroisoquinolin-2(1H)-yl)propan-2-olHCID 534066233-{1-[(Tert-butoxy)carbonyl]pyrrolidin-3-yl}benzoic acid

생성물 1

HCID 90241042tert-butyl 3-(3-((3-(3,4-dihydroisoquinolin-2(1H)-yl)-2-hydroxypropyl) carbamoyl)phenyl)pyrrolidine-1-carboxylate
수율 92%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

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온도
31 °C

실험 절차

To a solution of 3-(1-(tert-butoxycarbonyl)pyrrolidin-3-yl)benzoic acid (200 mg, 0.69 mmol) in DMF (4 ml) was added TEA (208 mg, 2.06 mmol), HOBt (139 mg, 1.03 mmol), EDCI (197 mg, 1.03 mmol) and 1-amino-3-(3,4-dihydroisoquinolin-2(1H)-yl)propan-2-ol (170 mg, 0.82 mmol) at 33° C. The reaction mixture was stirred for 16 h at 31° C. The mixture was treated with water and extracted with EA. The organic layer was washed with brine, dried over Na2SO4 and concentrated to give the title compound which was used in next step without further purification (300 mg, Yield 92%).

후처리

  1. extractionextracted with EA
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-3a07ce9eb8e14b6098b81014af7c64a7
출처 데이터셋
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08993555B2

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