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4-Methylmorpholine → 2-{(4-Fluoro-benzyl)-[2-(7-iodo-1,1-dioxo-1,4-dihydro-1lambda6 benzo[1,2,4]thiadiazin-3-yl)-acetyl]-amino}-cyclohexanecarboxylic acid ethyl ester

HRID 731364
ノート
印刷プレビュー

反応式

HRID 731364 の反応式
[I:1][C:2]1[CH:17]=[CH:16][C:5]2[NH:6][C:7]([CH2:12][C:13]([OH:15])=O)=[N:8][S:9](=[O:11])(=[O:10])[C:4]=2[CH:3]=1.[CH2:18]([O:20][C:21]([CH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH:24]1[NH:29][CH2:30][C:31]1[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=1)=[O:22])[CH3:19].Cl.CN(C)CCCN=C=NCC.CN1CCOCC1>CN(C)C=O.C(OCC)(=O)C>[CH2:18]([O:20][C:21]([CH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH:24]1[N:29]([CH2:30][C:31]1[CH:32]=[CH:33][C:34]([F:37])=[CH:35][CH:36]=1)[C:13](=[O:15])[CH2:12][C:7]1[NH:6][C:5]2[CH:16]=[CH:17][C:2]([I:1])=[CH:3][C:4]=2[S:9](=[O:10])(=[O:11])[N:8]=1)=[O:22])[CH3:19]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 79724-MethylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 576712242-(4-Fluoro-benzylamino)-cyclohexanecarboxylic acid ethyl esterHCID 59853574(7-Iodo-1,1-dioxo-1,4-dihydro-1lambda6-benzo[1,2,4]thiadiazin-3-yl)-acetic acid

生成物 1

HCID 57671204
2-{(4-Fluoro-benzyl)-[2-(7-iodo-1,1-dioxo-1,4-dihydro-1lambda6 benzo[1,2,4]thiadiazin-3-yl)-acetyl]-amino}-cyclohexanecarboxylic acid ethyl ester

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
25 °C

実験手順

(7-Iodo-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-3-yl)-acetic acid (prepared as described in Example 24b, 2.62 g, 7.16 mmol) was dissolved in anhydrous N,N-dimethylformamide (30 mL). 2-(4-Fluoro-benzylamino)-cyclohexanecarboxylic acid ethyl ester (2.0 g, 7.16 mmol) was added followed by 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.44 g, 7.52 mmol). Then N-methylmorpholine (1.52 g, 15.04 mmol) was added into the above reaction mixture. The mixture stirred at 25° C. for 24 h. The solution was diluted with ethyl acetate (200 mL), washed with 1.0 M aqueous hydrochloric acid solution, saturated aqueous sodium bicarbonate solution and saturated aqueous brine solution. The organic layer was dried over sodium sulfate and concentrated in vacuo to afford the crude product, 2-{(4-fluoro-benzyl)-[2-(7-iodo-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-3-yl)-acetyl]-amino}-cyclohexanecarboxylic acid ethyl ester, as a yellow oil, which was used directly in the next step without further purification. LC-MS (ESI) calcd for C25H27FIN3O5S 627.07, found 628.3 [M+H+].

後処理

  1. washwashed with 1.0 M aqueous hydrochloric acid solution, saturated aqueous sodium bicarbonate solution and saturated aqueous brine solution
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-96e73801e2634ad78840127ccbfbe53c
出典データセット
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07582626B2

反応ノート

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