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Water → 4-{4-[4-(1,1-Dioxo-tetrahydro-1lambda*6*-thiophen-3-ylmethoxy)-indol-1-yl]-pyrimidin-2-ylamino}-cyclohexanecarboxylic acid ethyl ester

HRID 237432
ノート
印刷プレビュー

反応式

HRID 237432 の反応式
[O:1]=[S:2]1(=[O:29])[CH2:6][CH2:5][CH:4]([CH2:7][O:8][C:9]2[CH:17]=[CH:16][CH:15]=[C:14]3[C:10]=2[CH:11]=[CH:12][N:13]3[C:18]2[CH:23]=[CH:22][N:21]=[C:20](S(CCC)=O)[N:19]=2)[CH2:3]1.Cl.[CH2:31]([O:33][C:34]([CH:36]1[CH2:41][CH2:40][CH:39]([NH2:42])[CH2:38][CH2:37]1)=[O:35])[CH3:32].C(N(C(C)C)CC)(C)C.O>CN1C(=O)CCC1>[CH2:31]([O:33][C:34]([CH:36]1[CH2:41][CH2:40][CH:39]([NH:42][C:20]2[N:19]=[C:18]([N:13]3[C:14]4[C:10](=[C:9]([O:8][CH2:7][CH:4]5[CH2:5][CH2:6][S:2](=[O:29])(=[O:1])[CH2:3]5)[CH:17]=[CH:16][CH:15]=4)[CH:11]=[CH:12]3)[CH:23]=[CH:22][N:21]=2)[CH2:38][CH2:37]1)=[O:35])[CH3:32]
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

6

反応物 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 11586508trans-Ethyl 4-aminocyclohexanecarboxylate hydrochlorideHCID 585421604-(1,1-dioxo-tetrahydro-1lambda*6*-thiophen-3-ylmethoxy)-1-[2-(propane-1-sulfinyl)-pyrimidin-4-yl]-1H-indole

生成物 1

HCID 585421644-{4-[4-(1,1-Dioxo-tetrahydro-1lambda*6*-thiophen-3-ylmethoxy)-indol-1-yl]-pyrimidin-2-ylamino}-cyclohexanecarboxylic acid ethyl ester
収率 75.3%

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
80 °C

実験手順

To a solution of 4-(1,1-dioxo-tetrahydro-1lambda*6*-thiophen-3-ylmethoxy)-1-[2-(propane-1-sulfinyl)-pyrimidin-4-yl]-1H-indole 1.2 g) and 4-amino-cyclohexanecarboxylic acid ethyl ester HCl salt (1.12 g) in NMP (5 mL) was added diisopropylethylamine (1.4 mL). The mixture was heated to 80° C. for 18 hours, then cooled and poured into 75 mL water. The mixture was extracted with methylene chloride, and the combined organic layers were dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (60% EtOAc in hexanes) to give 1.069 g of 4-{4-[4-(1,1-dioxo-tetrahydro-1lambda*6*-thiophen-3-ylmethoxy)-indol-1-yl]-pyrimidin-2-ylamino}-cyclohexanecarboxylic acid ethyl ester.

後処理

  1. temperaturecooled
  2. extractionThe mixture was extracted with methylene chloride
  3. dry with materialthe combined organic layers were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography (60% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-223da95480584a8ab75e90534097b2e8
出典データセット
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08642601B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート