Hydrochloric Acid → 1-(Adamant-1-yl)-3-[2-(4-[2-[4-(2,4-dioxothiazolidin-5-ylmethyl)phenoxymethyl]-1-methyl-1H-benzimidazol-6-yloxy]phenyl)ethyl]urea dihydrochloride

HRID 412349

反応式

HRID 412349 の反応式
[ClH:1].Cl.[NH2:3][CH2:4][CH2:5][C:6]1[CH:38]=[CH:37][C:9]([O:10][C:11]2[CH:12]=[CH:13][C:14]3[N:18]=[C:17]([CH2:19][O:20][C:21]4[CH:34]=[CH:33][C:24]([CH2:25][CH:26]5[S:30][C:29](=[O:31])[NH:28][C:27]5=[O:32])=[CH:23][CH:22]=4)[N:16]([CH3:35])[C:15]=3[CH:36]=2)=[CH:8][CH:7]=1.[C:39]12([N:49]=[C:50]=[O:51])[CH2:48][CH:43]3[CH2:44][CH:45]([CH2:47][CH:41]([CH2:42]3)[CH2:40]1)[CH2:46]2.C(N(CC)CC)C.Cl>O1CCCC1.O1CCOCC1.CN(C)C=O>[ClH:1].[ClH:1].[C:39]12([NH:49][C:50]([NH:3][CH2:4][CH2:5][C:6]3[CH:7]=[CH:8][C:9]([O:10][C:11]4[CH:12]=[CH:13][C:14]5[N:18]=[C:17]([CH2:19][O:20][C:21]6[CH:34]=[CH:33][C:24]([CH2:25][CH:26]7[S:30][C:29](=[O:31])[NH:28][C:27]7=[O:32])=[CH:23][CH:22]=6)[N:16]([CH3:35])[C:15]=5[CH:36]=4)=[CH:37][CH:38]=3)=[O:51])[CH2:48][CH:43]3[CH2:44][CH:45]([CH2:47][CH:41]([CH2:42]3)[CH2:40]1)[CH2:46]2

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 20599951-IsocyanatoadamantaneHCID 865877735-[4-[6-[4-(2-aminoethyl)phenoxy]-1-methyl-1H-benzimidazol-2-ylmethoxy]benzyl]thiazolidine-2,4-dione dihydrochloride

生成物 1

HCID 185376881-(Adamant-1-yl)-3-[2-(4-[2-[4-(2,4-dioxothiazolidin-5-ylmethyl)phenoxymethyl]-1-methyl-1H-benzimidazol-6-yloxy]phenyl)ethyl]urea dihydrochloride収率 152.9%

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒HCID 312751,4-Dioxane溶媒

実験手順

1-(Adamant-1-yl)-3-[2-(4-[2-[4-(2,4-dioxothiazolidin-5-ylmethyl)phenoxymethyl]-1-methyl-1H-benzimidazol-6-yloxy]phenyl)ethyl]urea was obtained by a similar procedure to that described in Example 31 using 5-[4-[6-[4-(2-aminoethyl)phenoxy]-1-methyl-1H-benzimidazol-2-ylmethoxy]benzyl]thiazolidine-2,4-dione dihydrochloride (0.3 g), 1-adamantyl isocyanate (94 mg), triethylamine (65 mg) and anhydrous N,N-dimethylformamide (15 ml). To a solution of the product in tetrahydrofuran (10 ml) was added 4N hydrogen chloride in dioxane (10 ml) and the mixture was stirred at room temperature for 3 hours. The precipitate was isolated by filtration and washed with tetrahydrofuran and n-hexane to afford the title compound (0.3 g, mp 174-176° C.).

後処理

  1. customThe precipitate was isolated by filtration
  2. washwashed with tetrahydrofuran and n-hexane

出典と根拠

ORDレコード
ord-2e03b5a62d5b47e390f1a3c32884a376
出典データセット
uspto-grants-2003_05
特許番号
US06562849B1

関連ノート

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