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 2403502

反応式

HRID 2403502 の反応式
[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

参加物

6

反応物 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

生成物 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-ylcarbamate収率 68.2%

試薬・触媒・溶媒 1

HCID 31374Dimethylacetamide溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-72e31cae4868478b94586beb42843a13
出典データセット
uspto-grants-2014_08
特許番号
US08802667B2

関連ノート

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