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Sodium Hydroxide → Methyl 3-fluoro-4-(2-(5-(methoxymethyl)pyridin-2-ylamino)thiazol-5-ylthio)picolinate

HRID 1685347
ノート
印刷プレビュー

反応式

HRID 1685347 の反応式
[CH3:1][O:2][CH2:3][C:4]1[CH:5]=[CH:6][C:7]([NH:10][C:11]2[S:12][C:13]([S:16][C:17]#N)=[CH:14][N:15]=2)=[N:8][CH:9]=1.SC[C@H]([C@@H](CS)O)O.ClC1[CH:33]=[CH:32][N:31]=[C:30]([C:34]([O:36][CH3:37])=[O:35])[C:29]=1[F:38].[OH-].[Na+]>CO>[F:38][C:29]1[C:30]([C:34]([O:36][CH3:37])=[O:35])=[N:31][CH:32]=[CH:33][C:17]=1[S:16][C:13]1[S:12][C:11]([NH:10][C:7]2[CH:6]=[CH:5][C:4]([CH2:3][O:2][CH3:1])=[CH:9][N:8]=2)=[N:15][CH:14]=1
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 14798Sodium HydroxideHCID 446094D-1,4-DithiothreitolHCID 59200355Methyl 4-chloro-3-fluoropicolinateHCID 59200492N-(5-(methoxymethyl)pyridin-2-yl)-5-thiocyanatothiazol-2-amine

生成物 1

HCID 59200467Methyl 3-fluoro-4-(2-(5-(methoxymethyl)pyridin-2-ylamino)thiazol-5-ylthio)picolinate収率 39%

試薬・触媒・溶媒 1

HCID 887
Methanol
溶媒

反応条件

温度
23 °C

実験手順

A suspension of N-(5-(methoxymethyl)pyridin-2-yl)-5-thiocyanatothiazol-2-amine (0.109 g, 0.392 mmol) in methanol (15 mL) was bubbled with argon for 10 minutes and then treated with dithiothreitol (0.079 g, 0.510 mmol). The reaction was stirred at 23° C. for 10 minutes, then methyl 4-chloro-3-fluoropicolinate (0.0743 g, 0.392 mmol) was added, followed by aq. NaOH (1N, 0.43 mL, 0.431 mmol). The resulting brown solution was stirred for 45 minutes, then concentrated to about one quarter of the volume, diluted in water (15 mL) and neutralized with aq. sat. ammonium chloride. The precipitate was filtered to give the crude title material (0.062 g, 39%) as a solid which was used as such in the next reaction. HPLC ret. time (Condition A): 1.625 min. LC/MS (M+H)+: 407.

後処理

  1. customwas bubbled with argon for 10 minutes
  2. stirringThe resulting brown solution was stirred for 45 minutes
  3. concentrationconcentrated to about one quarter of the volume
  4. additiondiluted in water (15 mL)
  5. filtrationThe precipitate was filtered

出典と根拠

ORDレコード
ord-e8ed54254a3948f1a4c0b8a6ec896a3c
出典データセット
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08148400B2

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