[2-(3-Cyclohexyl-3-phenethylureido)-thiazol-5-ylsulfanyl]-acetic acid → HCID 178472930、化合物

HRID 2043898ノート

反応式

HRID 2043898 の反応式
[CH2:1]([O:3][C:4](=[O:16])[CH2:5][NH:6][S:7]([C:10]1[S:14][C:13]([NH2:15])=[N:12][CH:11]=1)(=[O:9])=[O:8])[CH3:2].[CH3:17][CH:18]([CH3:29])[CH2:19][CH2:20][NH:21][CH:22]1[CH2:27][CH2:26][CH:25]([CH3:28])[CH2:24][CH2:23]1.C1(N(CCC2C=CC=CC=2)C(=O)NC2SC(SC[C:46](O)=[O:47])=CN=2)CCCCC1>CN(C1C=CN=CC=1)C.C1COCC1>[CH2:1]([O:3][C:4](=[O:16])[CH2:5][NH:6][S:7]([C:10]1[S:14][C:13]([NH:15][C:46]([N:21]([CH2:20][CH2:19][CH:18]([CH3:29])[CH3:17])[C@H:22]2[CH2:23][CH2:24][C@H:25]([CH3:28])[CH2:26][CH2:27]2)=[O:47])=[N:12][CH:11]=1)(=[O:8])=[O:9])[CH3:2]

参加物

6

反応物 3

HCID 11993791[2-(3-Cyclohexyl-3-phenethylureido)-thiazol-5-ylsulfanyl]-acetic acidHCID 213556364-methyl-N-(3-methylbutyl)cyclohexan-1-amineHCID 86253773(2-Amino-thiazole-5-sulfonylamino)acetic acid ethyl ester

生成物 1

HCID 178472930HCID 178472930、化合物

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
55 °C

実験手順

An equimolar mixture of 1,1-carbonyldiimidazole, (2-amino-thiazole-5-sulfonylamino)-acetic acid ethyl ester and DMAP (5 mol %) in THF was heated for 5 h at 50-60° C. and then cooled to room temperature. Then (3-methyl-butyl)-(4-methyl-cyclohexyl)-amine (1 equivalent; prepared following the procedure described in the preparation of [2-(3-cyclohexyl-3-phenethylureido)-thiazol-5-ylsulfanyl]-acetic acid) was added and the reaction is stirred overnight at room temperature. The reaction mixture was quenched with water. The organic phase was isolated and the aqueous phase was extracted with CH2Cl2, and the combined organic phases were dried and concentrated in vacuo. The crude product was dissolved in MeCN and purified using HPLC to give {2-[3-(3-methyl-butyl)-3-(trans-4-methyl-cyclohexyl)-ureido]-thiazole-5-sulfonylamino}-acetic acid ethyl ester as crystals.

後処理

  1. temperaturecooled to room temperature
  2. customprepared
  3. additionwas added
  4. customThe reaction mixture was quenched with water
  5. customThe organic phase was isolated
  6. extractionthe aqueous phase was extracted with CH2Cl2
  7. customthe combined organic phases were dried
  8. concentrationconcentrated in vacuo
  9. dissolutionThe crude product was dissolved in MeCN
  10. custompurified

出典と根拠

ORDレコード
ord-db205c7391d74f7388d201a05f4721f7
出典データセット
uspto-grants-2013_11
特許番号
US08586614B2

反応ノート

読み込み中…