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

HRID 1685053노트

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HRID 1685053 반응식
[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]

참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 3

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

반응 조건

온도
60 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-0ca05ccaa8d84add919c842cf41e17a6
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08148380B2

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