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Triethylamine → 3-(4-{4-[(1H-benzoimidazol-2-ylamino)methyl]piperidin-1-yl}phenyl)-2-(2,4,6-trimethylbenzoylamino)propionic acid

HRID 1424320
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HRID 1424320 반응식
FC(F)(F)C(O)=O.[NH:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[NH:17][CH2:18][CH:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1.B([C:28]1[CH:33]=[CH:32][C:31]([CH2:34][CH:35]([NH:39][C:40](=[O:50])[C:41]2[C:46]([CH3:47])=[CH:45][C:44]([CH3:48])=[CH:43][C:42]=2[CH3:49])[C:36]([OH:38])=[O:37])=[CH:30][CH:29]=1)(O)O.CCN(CC)CC>ClCCCl.CC([O-])=O.CC([O-])=O.[Cu+2]>[NH:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[NH:17][CH2:18][CH:19]1[CH2:24][CH2:23][N:22]([C:28]2[CH:33]=[CH:32][C:31]([CH2:34][CH:35]([NH:39][C:40](=[O:50])[C:41]3[C:42]([CH3:49])=[CH:43][C:44]([CH3:48])=[CH:45][C:46]=3[CH3:47])[C:36]([OH:38])=[O:37])=[CH:30][CH:29]=2)[CH2:21][CH2:20]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 576609483-(4-Boronophenyl)-2-(2,4,6-trimethylbenzoylamino)propionic acidHCID 69079613(1H-benzoimidazol-2-yl)piperidin-4-ylmethylamine trifluoroacetate

생성물 1

HCID 248721893-(4-{4-[(1H-benzoimidazol-2-ylamino)methyl]piperidin-1-yl}phenyl)-2-(2,4,6-trimethylbenzoylamino)propionic acid

시약·촉매·용매 2

HCID 8895
Cupric acetate
촉매
HCID 111,2-Dichloroethane용매

실험 절차

95 mg (0.207 mmol, calculated as bistrifluoroacetate salt) of crude piperidine derivative (19), 113 mg (0.621 mmol) Cu(OAc)2, 147 mg (0.415 mmol) boronic acid (6) and 1.72 ml (12.42 mmol) NEt3 were mixed in 10 ml DCE and stirred at room temperature for 20 h. The reaction mixture was concentrated under reduced pressure and the residue was dissolved in methanol and subsequently submitted to reversed phase HPLC purification using a water/acetonitrile gradient containing 0.1% TFA. The required fractions were collected and lyophilized to yield (20) as white solid.

후처리

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in methanol
  3. customphase HPLC purification
  4. additioncontaining 0.1% TFA
  5. customThe required fractions were collected

출처 및 근거

ORD 기록
ord-77abbd1afe25445aa857ff55be847c6d
출처 데이터셋
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08927534B2

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