Sodium Hydroxide → 1-[4-(Cyano-methylamino-methyl)-thiazol-2-yl]-3-(3-fluoro-benzyl)-urea

HRID 1685053ノート

反応式

HRID 1685053 の反応式
[F:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[CH2:5][NH:6][C:7]([NH:9][C:10]1[S:11][CH:12]=[C:13]([CH2:15]O)[N:14]=1)=[O:8].[NH2:20][C:21]1SC=C(COC(=O)C)N=1.FC1C=C(C=CC=1)[CH2:35][N:36]=C=O.[OH-].[Na+]>C1COCC1.CCOC(C)=O.CO>[C:21]([CH:15]([NH:36][CH3:35])[C:13]1[N:14]=[C:10]([NH:9][C:7]([NH:6][CH2:5][C:4]2[CH:17]=[CH:18][CH:19]=[C:2]([F:1])[CH:3]=2)=[O:8])[S:11][CH:12]=1)#[N:20]

参加物

8

反応物 4

HCID 14798Sodium HydroxideHCID 6434993-Fluorobenzyl isocyanateHCID 21915033Acetic acid 2-amino-thiazol-4-ylmethyl esterHCID 86661282(3-Fluoro-benzyl)-3-(4-hydroxymethyl-thiazol-2-yl)-urea

生成物 1

HCID 866613041-[4-(Cyano-methylamino-methyl)-thiazol-2-yl]-3-(3-fluoro-benzyl)-urea

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
60 °C

実験手順

Preparation of -(3-fluoro-benzyl)-3-(4-hydroxymethyl-thiazol-2-yl)-urea. To a solution of acetic acid 2-amino-thiazol-4-ylmethyl ester (6.89 g) in THF (50 mL) were 3-fluorobenzylisocyanate (5.50 g) and TEA (5.03 mL) added. The resultant solution was heated at 70° C. over 2 h. Then, MeOH (30 mL) and NaOH (6N, 15 mL) were added to the above solution. The reaction mixture was heated at 60° C. for 30 min After cooling down, the reaction mixture was diluted with EtOAc (150 mL) and was washed with water. The organic solvents were concentrated and the residue was purified by silica-gel column chromatography to afford 8.29 g of the desired product-1-(3-fluoro-benzyl)-3-(4-hydroxymethyl-thiazol-2-yl)-urea.

後処理

  1. additionadded
  2. temperatureAfter cooling down
  3. washwas washed with water
  4. concentrationThe organic solvents were concentrated
  5. customthe residue was purified by silica-gel column chromatography

出典と根拠

ORDレコード
ord-0ca05ccaa8d84add919c842cf41e17a6
出典データセット
uspto-grants-2012_04
特許番号
US08148380B2

反応ノート

読み込み中…