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Cyclopropanecarbonyl chloride → N-{[1-(Cyclopropylcarbonyl)piperidin-4-yl]methyl}-N'-{[(2S)-4-(3,4-dichlorobenzyl)morpholin-2-yl]methyl}urea

HRID 1371455
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HRID 1371455 반응식
[CH:1]1([C:4](Cl)=[O:5])[CH2:3][CH2:2]1.Cl.Cl.[Cl:9][C:10]1[CH:11]=[C:12]([CH:32]=[CH:33][C:34]=1[Cl:35])[CH2:13][N:14]1[CH2:19][CH2:18][O:17][C@@H:16]([CH2:20][NH:21][C:22]([NH:24][CH2:25][CH:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)=[O:23])[CH2:15]1.C(N(CC)C(C)C)(C)C>ClCCl>[CH:1]1([C:4]([N:29]2[CH2:30][CH2:31][CH:26]([CH2:25][NH:24][C:22]([NH:21][CH2:20][C@@H:16]3[O:17][CH2:18][CH2:19][N:14]([CH2:13][C:12]4[CH:32]=[CH:33][C:34]([Cl:35])=[C:10]([Cl:9])[CH:11]=4)[CH2:15]3)=[O:23])[CH2:27][CH2:28]2)=[O:5])[CH2:3][CH2:2]1
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참가 물질

5

반응물 3

HCID 77637Cyclopropanecarbonyl chlorideHCID 81531DiisopropylethylamineHCID 69507286HCID 69507286, 화합물

생성물 1

HCID 69507465N-{[1-(Cyclopropylcarbonyl)piperidin-4-yl]methyl}-N'-{[(2S)-4-(3,4-dichlorobenzyl)morpholin-2-yl]methyl}urea

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
23 °C

실험 절차

Cyclopropanecarbonyl chloride (0.014 ml) was added to a solution of Intermediate 18 (0.54 g) and N,N-diisopropylethylamine (0.063 ml) in dichloromethane (2 ml). The solution was stirred for 3 h at 23° C. The solvent was removed in vacuo and the residue purified by solid phase extraction (Isolute SCX sulphonic acid column) eluting with methanol followed by 10% 0.880 ammonia solution in methanol. The basic fraction was concentrated in vacuo and the residue was further purified using a silica gel solid phase extraction cartridge (1 g Varian Bond Elut) eluting with 0–1% methanol in ethyl acetate, to give the title compound as a clear gum (0.023 g).

후처리

  1. customThe solvent was removed in vacuo
  2. customthe residue purified by solid phase extraction (Isolute SCX sulphonic acid column)
  3. washeluting with methanol
  4. concentrationThe basic fraction was concentrated in vacuo
  5. customthe residue was further purified
  6. extractiona silica gel solid phase extraction cartridge (1 g Varian Bond Elut)
  7. washeluting with 0–1% methanol in ethyl acetate

출처 및 근거

ORD 기록
ord-a509d44ee9ce4d188a3b0244b8fa2d94
출처 데이터셋
uspto-grants-2007_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07157457B2

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