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Dimethylformamide → (S)-2-amino-N-(4-(3-(piperidin-4-yloxy)phenyl)but-3-ynyl)pent-4-ynamide

HRID 473520
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HRID 473520 반응식
[C:1]1([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:6]=[CH:5][CH:4]=C(C#CCCCN)C=1.C(OC([NH:26][CH:27]([CH2:31][C:32]#[CH:33])[C:28]([OH:30])=O)=O)(C)(C)C.C1C=CC2N(O)N=NC=2C=1.CC[N:46]=C=NCCCN(C)C.Cl.CC[N:58]([CH:62]([CH3:64])C)[CH:59]([CH3:61])C.CN([CH:68]=[O:69])C>>[NH2:26][C@@H:27]([CH2:31][C:32]#[CH:33])[C:28]([NH:46][CH2:4][CH2:5][C:6]#[C:1][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]([O:69][CH:68]2[CH2:61][CH2:59][NH:58][CH2:62][CH2:64]2)[CH:18]=1)=[O:30]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 6

HCID 6228DimethylformamideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 35131712-((Tert-butoxycarbonyl)amino)pent-4-ynoic acidHCID 672035705-(Biphenyl-3-yl)pent-4-yn-1-amine

생성물 1

HCID 52919716
(S)-2-amino-N-(4-(3-(piperidin-4-yloxy)phenyl)but-3-ynyl)pent-4-ynamide

실험 절차

5-(Biphenyl-3-yl)pent-4-yn-1-amine (0.040 g, 0.17 mmol), 2-tert-Butoxycarbonylamino-pent-4-ynoic acid (40 mg, 0.19 mmol), HOBt (28 mg, 0.21 mmol), EDCl (40 mg, 0.21 mmol), and DIEA (0.044 mL, 0.25 mmol) were taken into DMF (3 mL) and stirred at room temperature overnight. The reaction was then quenched with water and the resulting mixture extracted with EtOAc. The organic layer was washed with saturated NaHCO3 and brine, then dried over sodium sulfate and the solvent removed in vacuo. The resulting residue was taken up into DCM/TFA (4/1, 5 mL) and the resulting mixture was stirred at room temp for 1 hr. The solvent was removed in vacuo and prepped on the Gilson HPLC to yield the title compound, as its corresponding TFA salt. MH+ 331.2; 1H NMR (300 MHz, DMSO): δ 1.6-1.8 (m, 3H), 2.45 (m, 2H), 2.7 (s, 2H), 3.2-3.4 (m, 2H), 3.9 (s, 1H), 7.3-7.4 (m, 5H), 7.6-7.7 (m, 4H), 8.3 (s, 2H), 8.6 (s, 1H)

후처리

  1. customThe reaction was then quenched with water
  2. extractionthe resulting mixture extracted with EtOAc
  3. washThe organic layer was washed with saturated NaHCO3 and brine
  4. dry with materialdried over sodium sulfate
  5. customthe solvent removed in vacuo
  6. stirringthe resulting mixture was stirred at room temp for 1 hr
  7. customThe solvent was removed in vacuo

출처 및 근거

ORD 기록
ord-50428b495bf34bde8b4bf5df23e3e766
출처 데이터셋
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08633322B2

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