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Diisopropylethylamine → tert-butyl (2-(4-((2S,4R)-1-acetyl-4-((5-cyanopyridin-2-yl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)benzamido)ethyl)carbamate

HRID 882245
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HRID 882245 반응식
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3[CH:22]=[CH:21][C:17]([C:18](O)=[O:19])=[CH:16][CH:15]=3)=[CH:11][CH:12]=2)[C@H:7]([NH:23][C:24]2[CH:29]=[CH:28][C:27]([C:30]#[N:31])=[CH:26][N:25]=2)[CH2:6][C@@H:5]1[CH3:32])(=[O:3])[CH3:2].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[NH2:66][CH2:67][CH2:68][NH:69][C:70](=[O:76])[O:71][C:72]([CH3:75])([CH3:74])[CH3:73]>CN(C=O)C>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3[CH:22]=[CH:21][C:17]([C:18]([NH:66][CH2:67][CH2:68][NH:69][C:70](=[O:76])[O:71][C:72]([CH3:74])([CH3:73])[CH3:75])=[O:19])=[CH:16][CH:15]=3)=[CH:11][CH:12]=2)[C@H:7]([NH:23][C:24]2[CH:29]=[CH:28][C:27]([C:30]#[N:31])=[CH:26][N:25]=2)[CH2:6][C@@H:5]1[CH3:32])(=[O:3])[CH3:2]
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참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 187201N-BOC-ethylenediamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 709764624-((2S,4R)-1-acetyl-4-((5-cyanopyridin-2-yl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)benzoic acid

생성물 1

HCID 86709419
tert-butyl (2-(4-((2S,4R)-1-acetyl-4-((5-cyanopyridin-2-yl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)benzamido)ethyl)carbamate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a flask charged with 4-((2S,4R)-1-acetyl-4-((5-cyanopyridin-2-yl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)benzoic acid (for a preparation see Intermediate 4)((70 mg, 0.164 mmol) and HATU (74.9 mg, 0.197 mmol) was added DMF (3 mL) and the resulting mixture was treated with DIPEA (0.086 mL, 0.492 mmol). After 5 min, tert-butyl (2-aminoethyl)carbamate (52.6 mg, 0.328 mmol) was added and the mixture was stirred at room temperature for 1 h and then concentrated in vacuo. The residue was partitioned between EtOAc and water and the layers were separated. The aqueous phase was extracted with EtOAc (×2) and the combined organic layers were washed with saturated aqueous NaHCO3 (×3), then brine, dried over MgSO4 and concentrated in vacuo to give tert-butyl (2-(4-((2S,4R)-1-acetyl-4-((5-cyanopyridin-2-yl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)benzamido)ethyl)carbamate as a brown foam which was further purified by MDAP (HpH). to give tert-butyl (2-(4-((2S,4R)-1-acetyl-4-((5-cyanopyridin-2-yl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)benzamido)ethyl)carbamate (65 mg, 0.114 mmol, 69.6% yield) as a white solid. LCMS (HpH, 2 min), Rt=1.00 min, MH+=569.

후처리

  1. concentrationconcentrated in vacuo
  2. customThe residue was partitioned between EtOAc and water
  3. customthe layers were separated
  4. extractionThe aqueous phase was extracted with EtOAc (×2)
  5. washthe combined organic layers were washed with saturated aqueous NaHCO3 (×3)
  6. dry with materialbrine, dried over MgSO4
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-66321e2b1ade44ea9898f82c05576c55
출처 데이터셋
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08993554B2

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