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Diisopropylethylamine → N-{2-[4-(2-Butyl-4-chloro-5-formylimidazol-1-ylmethyl)benzenesulfonylamino]-2-oxoethyl}-N'-(2,2-dimethylpropionyloxy)-2-isobutylmalonamide

HRID 1669549
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HRID 1669549 반응식
[NH2:1][CH2:2][C:3]([NH:5][S:6]([C:9]1[CH:14]=[CH:13][C:12]([CH2:15][N:16]2[C:20]([CH:21]=[O:22])=[C:19]([Cl:23])[N:18]=[C:17]2[CH2:24][CH2:25][CH2:26][CH3:27])=[CH:11][CH:10]=1)(=[O:8])=[O:7])=[O:4].[CH3:28][C:29]([CH3:45])([CH3:44])[C:30]([O:32][NH:33][C:34]([CH:36]([CH2:40][CH:41]([CH3:43])[CH3:42])[C:37](O)=[O:38])=[O:35])=[O:31].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O>[CH2:24]([C:17]1[N:16]([CH2:15][C:12]2[CH:13]=[CH:14][C:9]([S:6]([NH:5][C:3](=[O:4])[CH2:2][NH:1][C:37](=[O:38])[CH:36]([CH2:40][CH:41]([CH3:42])[CH3:43])[C:34]([NH:33][O:32][C:30](=[O:31])[C:29]([CH3:44])([CH3:45])[CH3:28])=[O:35])(=[O:7])=[O:8])=[CH:10][CH:11]=2)[C:20]([CH:21]=[O:22])=[C:19]([Cl:23])[N:18]=1)[CH2:25][CH2:26][CH3:27]
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참가 물질

7

반응물 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57931395N-(2-Aminoacetyl)-4-(2-butyl-4-chloro-5-formyl-imidazol-1-ylmethyl)benzenesulfonamideHCID 594288372-(2,2-Dimethylpropionyloxycarbamoyl)-4-methylpentanoic acid

생성물 1

HCID 86635446
N-{2-[4-(2-Butyl-4-chloro-5-formylimidazol-1-ylmethyl)benzenesulfonylamino]-2-oxoethyl}-N'-(2,2-dimethylpropionyloxy)-2-isobutylmalonamide

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

N-(2-Aminoacetyl)-4-(2-butyl-4-chloro-5-formyl-imidazol-1-ylmethyl)benzenesulfonamide (770 mg, 1.2 mmol, 1.0 eq) and 2-(2,2-Dimethylpropionyloxycarbamoyl)-4-methylpentanoic acid (360 mg, 1.2 mmol, 1.0 eq) were dissolved in 13 mL DMF. HATU (460 mg, 1.2 mmol, 1.0 eq) was then added followed by DIPEA (630 μL, 3.6 mmol, 3.0 eq) and the mixture was stirred at room temperature. After 3 hours, the mixture was diluted with 30 mL EtOAc, washed with 20 mL 10% aq. LiCl solution, water, saturated aqueous NaCl, dried over MgSO4, filtered, and concentrated under reduced pressure to yield crude intermediate 3a. MS m/z: [M+H+] calcd for C29H40ClN5O8S, 654.2; found 654.4.

후처리

  1. washwashed with 20 mL 10% aq. LiCl solution, water, saturated aqueous NaCl
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-4b4ee07051f74a5ca9bcdad69740e884
출처 데이터셋
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07989484B2

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