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Diisopropylethylamine → tert-butyl 7-({(1S)-1-[4-(methoxycarbonyl)phenyl]ethyl}carbamoyl)indoline-1-carboxylate

HRID 646180
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HRID 646180 반응식
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][C:15]=2[C:17](O)=[O:18])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[Cl-].[CH3:45][O:46][C:47]([C:49]1[CH:54]=[CH:53][C:52]([C@@H:55]([NH3+:57])[CH3:56])=[CH:51][CH:50]=1)=[O:48].CCN(C(C)C)C(C)C>C(#N)C>[CH3:45][O:46][C:47]([C:49]1[CH:54]=[CH:53][C:52]([C@@H:55]([NH:57][C:17]([C:15]2[CH:14]=[CH:13][CH:12]=[C:11]3[C:16]=2[N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9][CH2:10]3)=[O:18])[CH3:56])=[CH:51][CH:50]=1)=[O:48]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 14977845N-Boc-indoline-7-carboxylic acidHCID 161770108[(1S)-1-(4-methoxycarbonylphenyl)ethyl]azanium chloride

생성물 1

HCID 58125255tert-butyl 7-({(1S)-1-[4-(methoxycarbonyl)phenyl]ethyl}carbamoyl)indoline-1-carboxylate

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

1-(tert-butoxycarbonyl)indoline-7-carboxylic acid (0.5 g, 1.9 mmol), HATU (795 mg, 2.09 mmol) and (1S)-1-[4-(methoxycarbonyl)phenyl]ethanaminium chloride (511 mg, 2.85 mmol) were added to acetonitrile (12.7 ml). The solution was cooled in an ice bath and DIPEA (993 ul, 5.7 mmol) was added. The ice bath was removed and the mixture stirred for 2 hours at RT. The solvent was removed and the crude mixture purified by flash chromatography on silica gel. 1H NMR (500 MHz, DMSO-d6): δ 8.40 (d, 1H), 7.90 (d, 2H), 7.55 (d, 2H), 7.30 (d, 1H), 7.25 (d, 1H), 7.00 (t, 1H), 5.10 (m, 1H), 4.00 (m, 2H), 3.85 (s, 3H), 3.05 (m, 2H), 1.45 (d, 3H), 1.40 (s, 9H).

후처리

  1. temperatureThe solution was cooled in an ice bath
  2. customThe ice bath was removed
  3. customThe solvent was removed
  4. customthe crude mixture purified by flash chromatography on silica gel

출처 및 근거

ORD 기록
ord-80c6e4df44d1416a96c6a608a50359a6
출처 데이터셋
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07705035B2

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