1,2-Dichloroethane → tert-Butyl 1-methyl-5-(1-methyl-2-(1-methyl-5-(1-methyl-5-(2-(pyridin-2-yldisulfanyl)ethylcarbamoyl)-1H-pyrrol-3-ylcarbamoyl)-1H-pyrrol-3-ylcarbamoyl)-1H-imidazol-4-ylcarbamoyl)-1H-pyrrol-3-ylcarbamate

HRID 1968495

반응식

HRID 1968495 반응식
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[C:11]([C:15]([NH:17][C:18]2[N:19]=[C:20]([C:24]([NH:26][C:27]3[CH:28]=[C:29]([C:33]([NH:35][C:36]4[CH:37]=[C:38]([C:42]([OH:44])=O)[N:39]([CH3:41])[CH:40]=4)=[O:34])[N:30]([CH3:32])[CH:31]=3)=[O:25])[N:21]([CH3:23])[CH:22]=2)=[O:16])[N:12]([CH3:14])[CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[N:46]1[CH:51]=[CH:50][CH:49]=[CH:48][C:47]=1[S:52][S:53][CH2:54][CH2:55][NH2:56].CCN(C(C)C)C(C)C.C(Cl)CCl>CC(N(C)C)=O>[CH3:14][N:12]1[C:11]([C:15](=[O:16])[NH:17][C:18]2[N:19]=[C:20]([C:24](=[O:25])[NH:26][C:27]3[CH:28]=[C:29]([C:33](=[O:34])[NH:35][C:36]4[CH:37]=[C:38]([C:42](=[O:44])[NH:56][CH2:55][CH2:54][S:53][S:52][C:47]5[CH:48]=[CH:49][CH:50]=[CH:51][N:46]=5)[N:39]([CH3:41])[CH:40]=4)[N:30]([CH3:32])[CH:31]=3)[N:21]([CH3:23])[CH:22]=2)=[CH:10][C:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[CH:13]1

참가 물질

6

반응물 4

HCID 111,2-DichloroethaneHCID 81531DiisopropylethylamineHCID 139852342-((2-Aminoethyl)disulfanyl)pyridine hydrochlorideHCID 594400974-(4-(4-(4-(tert-butoxycarbonylamino)-1-methyl-1H-pyrrole-2-carboxamido)-1-methyl-1H-imidazole-2-carboxamido)-1-methyl-1H-pyrrole-2-carboxamido)-1-methyl-1H-pyrrole-2-carboxylic acid

생성물 1

HCID 86644084tert-Butyl 1-methyl-5-(1-methyl-2-(1-methyl-5-(1-methyl-5-(2-(pyridin-2-yldisulfanyl)ethylcarbamoyl)-1H-pyrrol-3-ylcarbamoyl)-1H-pyrrol-3-ylcarbamoyl)-1H-imidazol-4-ylcarbamoyl)-1H-pyrrol-3-ylcarbamate수율 68.2%

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매

실험 절차

4-(4-(4-(4-(tert-butoxycarbonylamino)-1-methyl-1H-pyrrole-2-carboxamido)-1-methyl-1H-imidazole-2-carboxamido)-1-methyl-1H-pyrrole-2-carboxamido)-1-methyl-1H-pyrrole-2-carboxylic acid (102 mg, 0.17 mmol), 2-(pyridin-2-yldisulfanyl)ethanamine hydrogen chloride salt (40 mg, 0.18 mmol), DIPEA (30 ul, 0.17 mmol) and EDC (200 mg, 1.04 mmol) in 2 ml of DMA were stirred under Ar for 24 h, evaporated and purified on SiO2 chromatography eluted with THF/DCM (1:5 to 1:4) to afford 90 mg (68%) of the title compound. 1H NMR (DMSO) 10.93 (s, 1H), 10.19 (s, 1H), 10.06 (s, 1H), 9.03 (s, 1H), 8.81 (m 1H), 8.29 (m, 1H), 8.03 (m, 1H), 7.68 (s, 1H), 7.47 (s, 1H), 7.28 (s, 1H), 7.24 (s, 1H), 7.18 (m, 1H), 6.87 (s, 1H), 3.96 (s, 1H), 3.86 (s, 3H), 3.75 (s, 3H), 3.73 (s, 3H), 3.58 (m, 2H), 2.48 (m, 2H), 1.45 (s, 9H); MS m/z+ 798.0 (M+Na), 776.0 (M+H).

후처리

  1. customevaporated
  2. custompurified on SiO2 chromatography
  3. washeluted with THF/DCM (1:5 to 1:4)

출처 및 근거

ORD 기록
ord-4618f5dbf67d48f6972232ccdb8c250c
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08426402B2

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