N-(4-Amino-o-tolyl)-4-chlorophthalimide → {[(5-Chloro(2-thienyl))methyl]amino}-n-[4-(5-chloro-1,3-dioxobenzo[c]azolidin-2-yl)-3-methylphenyl]carboxamide

HRID 900266

反応式

HRID 900266 の反応式
Cl[C:2](Cl)([O:4]C(=O)OC(Cl)(Cl)Cl)Cl.[NH2:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]2[C:24](=[O:25])[C:23]3=[CH:26][C:27]([Cl:30])=[CH:28][CH:29]=[C:22]3[C:21]2=[O:31])=[C:16]([CH3:32])[CH:15]=1.[Cl:33][C:34]1[S:38][C:37]([CH2:39][NH2:40])=[CH:36][CH:35]=1>C(Cl)Cl.C(N(CC)C(C)C)C.CCN(C(C)C)C(C)C>[Cl:33][C:34]1[S:38][C:37]([CH2:39][NH:40][C:2]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([N:20]3[C:24](=[O:25])[C:23]4[CH:26]=[C:27]([Cl:30])[CH:28]=[CH:29][C:22]=4[C:21]3=[O:31])=[C:16]([CH3:32])[CH:15]=2)=[O:4])=[CH:36][CH:35]=1

参加物

7

反応物 3

HCID 93991N-(4-Amino-o-tolyl)-4-chlorophthalimideHCID 94429TriphosgeneHCID 11446421(5-Chlorothiophen-2-yl)methanamine

生成物 1

HCID 20799230{[(5-Chloro(2-thienyl))methyl]amino}-n-[4-(5-chloro-1,3-dioxobenzo[c]azolidin-2-yl)-3-methylphenyl]carboxamide収率 52.8%

試薬・触媒・溶媒 3

HCID 6344Dichloromethane溶媒3 回HCID 81531Diisopropylethylamine溶媒HCID 521913N,N-Diethyl-2-propanamine溶媒

実験手順

To a solution of triphosgene (22 mg, 0.074 mmol) in CH2Cl2 (1 mL) was added a suspension of N-(4-amino-2-methylphenyl)-4-chlorophthalimide (57 mg, 0.2 mmol) in CH2Cl2 (1.5 mL) and diethylisopropylamine (70 μL) dropwise over 10 min. The reaction mixture was stirred for 10 min, then a solution (5-chloro-2-thienyl)methylamine from step B (47 mg, 0.32 mmol) in CH2Cl2 (1 mL) and DIEA (35 μL) was added. The mixture was stirred at room temp for 17 hr, acidified and HPLC purified to give {[(5-chloro(2-thienyl))methyl]amino}-N-[4-(5-chloro-1,3-dioxobenzo[c]azolidin-2-yl)-3-methylphenyl]carboxamide (18 mg, 20%). ES-MS (M+H)+=460, 462 (Cl). 1H-NMR (DMSO-d6): δ 2.02 (s, 3H), 4.34-4.36 (d, 2H), 6.77-6.80 (t, 1H), 6.82-6.93 (2d, 2H), 7.14-7.16 (d, 1H), 7.29-7.32 (dd, 1H), 7.41 (d, 1H), 7.93 (ABq, 2H), 8.02 (s, 1H), 8.77 (s, 1H).

後処理

  1. stirringThe mixture was stirred at room temp for 17 hr
  2. customHPLC purified

出典と根拠

ORDレコード
ord-b01010bf0646406c876361049ea547cd
出典データセット
uspto-grants-2008_04
特許番号
US07358257B2

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