Propiolic Acid → N-{1-[(2S)-2-((3S)-3-{[(6-Chloro-2-naphthyl)sulfonyl]amino}-2-oxopyrrolidin-1-yl)propanoyl]piperidin-3-yl}prop-2-ynamide

HRID 1765653

반응식

HRID 1765653 반응식
[NH2:1][CH:2]1[CH2:7][CH2:6][CH2:5][N:4]([C:8](=[O:32])[C@@H:9]([N:11]2[CH2:15][CH2:14][C@H:13]([NH:16][S:17]([C:20]3[CH:29]=[CH:28][C:27]4[C:22](=[CH:23][CH:24]=[C:25]([Cl:30])[CH:26]=4)[CH:21]=3)(=[O:19])=[O:18])[C:12]2=[O:31])[CH3:10])[CH2:3]1.[C:33](O)(=[O:36])[C:34]#[CH:35].C(N(CC)C(C)C)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[Cl:30][C:25]1[CH:26]=[C:27]2[C:22](=[CH:23][CH:24]=1)[CH:21]=[C:20]([S:17]([NH:16][C@H:13]1[CH2:14][CH2:15][N:11]([C@@H:9]([CH3:10])[C:8]([N:4]3[CH2:5][CH2:6][CH2:7][CH:2]([NH:1][C:33](=[O:36])[C:34]#[CH:35])[CH2:3]3)=[O:32])[C:12]1=[O:31])(=[O:19])=[O:18])[CH:29]=[CH:28]2

참가 물질

6

반응물 4

HCID 10110Propiolic AcidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 69329851N-((3S)-1-[(1S)-2-(3-aminopiperidin-1-yl)-1-methyl-2-oxoethyl]-2-oxopyrrolidin-3-yl)-6-chloronaphthalene-2-sulfonamide

생성물 1

HCID 10165402N-{1-[(2S)-2-((3S)-3-{[(6-Chloro-2-naphthyl)sulfonyl]amino}-2-oxopyrrolidin-1-yl)propanoyl]piperidin-3-yl}prop-2-ynamide수율 115.5%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of N-{(3S)-1-[(1S)-2-(3-aminopiperidin-1-yl)-1-methyl-2-oxoethyl]-2-oxopyrrolidin-3-yl}-6-chloronaphthalene-2-sulfonamide (0.005 g) in DMF (0.5 ml) were added propiolic acid (0.001 g), N,N-diisopropylethylamine (0.0044 ml) and o-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (0.0049 ). The mixture was stirred at room temperature for 18 h and then concentrated under reduced pressure. The residue was partitioned between DCM and saturated sodium bicarbonate solution and then passed through a hydrophobic frit. The separated organic fraction was concentrated under reduced pressure to give the title compound (0.0064 g) as an oil.

후처리

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was partitioned between DCM and saturated sodium bicarbonate solution
  3. concentrationThe separated organic fraction was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-d8bb6034d9e54fd39ed97b94de4e9ddc
출처 데이터셋
uspto-grants-2007_06
특허 번호
US07226929B2

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