1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → (E)-4-(4-Methoxybenzyl)-7-(3-oxo-3-(3-(thiophen-2-ylmethoxy)azetidin-1-yl)prop-1-enyl)-4,5-dihydro-1H-pyrido[2,3-e][1,4]diazepin-2(3H)-one

HRID 83013

반응식

HRID 83013 반응식
Cl.[S:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[CH2:7][O:8][CH:9]1[CH2:12][NH:11][CH2:10]1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.C(N(C(C)C)CC)(C)C.Cl.[CH3:44][O:45][C:46]1[CH:69]=[CH:68][C:49]([CH2:50][N:51]2[CH2:57][C:56]3[CH:58]=[C:59](/[CH:62]=[CH:63]/[C:64](O)=[O:65])[CH:60]=[N:61][C:55]=3[NH:54][C:53](=[O:67])[CH2:52]2)=[CH:48][CH:47]=1>CN(C)C=O.O.C(OCC)(=O)C>[CH3:44][O:45][C:46]1[CH:69]=[CH:68][C:49]([CH2:50][N:51]2[CH2:57][C:56]3[CH:58]=[C:59](/[CH:62]=[CH:63]/[C:64](=[O:65])[N:11]4[CH2:12][CH:9]([O:8][CH2:7][C:3]5[S:2][CH:6]=[CH:5][CH:4]=5)[CH2:10]4)[CH:60]=[N:61][C:55]=3[NH:54][C:53](=[O:67])[CH2:52]2)=[CH:48][CH:47]=1

참가 물질

9

반응물 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 66966837HCID 66966837, 화합물HCID 671545443-(2-Thienylmethoxy)azetidine hydrochloride

생성물 1

HCID 68307379(E)-4-(4-Methoxybenzyl)-7-(3-oxo-3-(3-(thiophen-2-ylmethoxy)azetidin-1-yl)prop-1-enyl)-4,5-dihydro-1H-pyrido[2,3-e][1,4]diazepin-2(3H)-one수율 40%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

3-(Thiophen-2-ylmethoxy)-azetidine hydrochloride (231 mg, 1.12 mmol), EDCI (215 mg, 1.12 mmol), HOBt (152 mg, 1.12 mmol) and diisopropylethylamine (321 μL, 1.87 mmol) were successively added to a solution of (E)-3-(4-(4-methoxybenzyl)-2-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)acrylic acid hydrochloride (292 mg, 0.75 mmol) in dimethylformamide (20 mL) at room temperature. The reaction mixture was stirred overnight and then diluted by addition of ethyl acetate (30 ml) and water (30 mL). The aqueous layer was separated and extracted with ethyl acetate (2×30 mL) and dichloromethane (2×20 mL). The combined organic phases were washed with a saturated solution of sodium chloride (3×20 mL), dried over sodium sulfate, filtered and concentrated to dryness. The residue was precipitated from a mixture ethyl acetate/diethyl ether to afford the title product as an off-white solid (151 mg, 40%).

후처리

  1. customThe aqueous layer was separated
  2. extractionextracted with ethyl acetate (2×30 mL) and dichloromethane (2×20 mL)
  3. washThe combined organic phases were washed with a saturated solution of sodium chloride (3×20 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness
  7. customThe residue was precipitated from a mixture ethyl acetate/diethyl ether

출처 및 근거

ORD 기록
ord-a5cfe639891244d0ac9900216e8a9bd5
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846711B2

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