Triphenylphosphine → N-(2-benzyloxy-5-oxotetrahydrofuran-3-yl)-6,10-dioxo-9-(isoquinolin-1-oylamino)-1,2,3,4,7,8,9,10-octahydro-6-H-pyridazino[1,2-a][1,2]diazepine-1-carboxamide

HRID 988029노트

반응식

HRID 988029 반응식
C(O[C:5]([NH:7][C@H:8]1[CH2:12][C:11](=[O:13])[O:10][CH:9]1[O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:6])C=C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:41]1([C:51]([NH:53][CH:54]2[C:60](=[O:61])[N:59]3[CH:62](C([O-])=O)[CH2:63][CH2:64][CH2:65][N:58]3[C:57](=[O:69])[CH2:56][CH2:55]2)=[O:52])[C:50]2[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=2)[CH:44]=[CH:43][N:42]=1.OC1C2N=NNC=2C=CC=1.Cl.CN(C)CCCN=C=NCC>ClCCl.O>[CH2:15]([O:14][CH:9]1[CH:8]([NH:7][C:5]([CH:62]2[N:59]3[C:60](=[O:61])[CH:54]([NH:53][C:51]([C:41]4[C:50]5[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=5)[CH:44]=[CH:43][N:42]=4)=[O:52])[CH2:55][CH2:56][C:57](=[O:69])[N:58]3[CH2:65][CH2:64][CH2:63]2)=[O:6])[CH2:12][C:11](=[O:13])[O:10]1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

참가 물질

8

반응물 5

HCID 11776TriphenylphosphineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10989944(3S,2RS)3-allyloxycarbonylamino-2-benzyloxy-5-oxotetrahydrofuranHCID 867592179-(isoquinolin-1-oylamino)-6,10-dioxo-1,2,3,4,7,8,9, 10-octahydro-6-H-pyridazino[1,2-a][1,2]diazepine-1-carboxylateHCID 178418300HCID 178418300, 화합물

생성물 1

HCID 72754309N-(2-benzyloxy-5-oxotetrahydrofuran-3-yl)-6,10-dioxo-9-(isoquinolin-1-oylamino)-1,2,3,4,7,8,9,10-octahydro-6-H-pyridazino[1,2-a][1,2]diazepine-1-carboxamide

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

To a solution of (3S, 2RS) 3-allyloxycarbonylamino-2-benzyloxy-5-oxotetrahydrofuran [Bioorg. & Med. Chem. Lett., 2, pp. 615-618 (1992)] (4.4 g, 15.1 mmol) in dichloromethane was added N,N-dimethylbarbituric acid (5.9 g, 3.8 mmol) then tetrakispalladium(0) triphenyl phosphine (1.7 g, 1.5 mmol) and the resulting mixture was allowed to stir at ambient temperature for 15 minutes. To the resulting mixture was added the acid, compound XIII (from step C) (5.0 g, 12.6 mmol), hydroxybenzotriazole(2.0 g, 14.8 mmol), then 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (2.7 g, 14 mmol) and the reaction was allowed to stir for 3 hours at ambient temperature. The reaction mixture was then poured into water and extracted with ethyl acetate. The organics were washed with 0.5M sodium bisulfate, water, sodium bicarbonate, brine, dried over magnesium sulfate and concentrated in vacuo to afford 2.6 g of the crude product as a yellow foam. The crude material was purified by column chromatography (SiO2, dichloromethane:acetone 9:1-3:1) to afford 1.2 g of the compound 4-b.

후처리

  1. stirringto stir for 3 hours at ambient temperature
  2. extractionextracted with ethyl acetate
  3. washThe organics were washed with 0.5M sodium bisulfate, water, sodium bicarbonate, brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customto afford 2.6 g of the crude product as a yellow foam
  7. customThe crude material was purified by column chromatography (SiO2, dichloromethane:acetone 9:1-3:1)

출처 및 근거

ORD 기록
ord-98b6db93231b4d0ead9f86a38facab65
출처 데이터셋
uspto-grants-2003_10
특허 번호
US06632942B2

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