Trifluoroacetic acid → 1-[2-(4-Fluoro-3-trifluoromethyl-benzylamino)-ethyl]-3-(7-methoxy-thiazolo[5,4-d]pyrimidin-2-yl)-urea

HRID 550831

反応式

HRID 550831 の反応式
FC(F)(F)C(O)=O.[CH3:8][O:9][C:10]1[C:11]2[N:18]=[C:17]([NH:19][C:20]([N:22]3CC[CH:24]([NH2:27])[CH2:23]3)=[O:21])[S:16][C:12]=2[N:13]=[CH:14][N:15]=1.[F:28][C:29]1[CH:36]=[CH:35][C:32]([CH:33]=O)=[CH:31][C:30]=1[C:37]([F:40])([F:39])[F:38].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(N(CC)CC)C>CO>[F:28][C:29]1[CH:36]=[CH:35][C:32]([CH2:33][NH:27][CH2:24][CH2:23][NH:22][C:20]([NH:19][C:17]2[S:16][C:12]3[N:13]=[CH:14][N:15]=[C:10]([O:9][CH3:8])[C:11]=3[N:18]=2)=[O:21])=[CH:31][C:30]=1[C:37]([F:38])([F:39])[F:40]

参加物

7

反応物 5

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 5222694-Fluoro-3-(trifluoromethyl)benzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 724893723-Amino-pyrrolidine-1-carboxylic acid (7-methoxy-thiazolo[5,4-d]pyrimidin-2-yl)-amide

生成物 1

HCID 590119711-[2-(4-Fluoro-3-trifluoromethyl-benzylamino)-ethyl]-3-(7-methoxy-thiazolo[5,4-d]pyrimidin-2-yl)-urea収率 18.1%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
25 °C

実験手順

A solution of the trifluoroacetic acid salt of 3-amino-pyrrolidine-1-carboxylic acid (7-methoxy-thiazolo[5,4-d]pyrimidin-2-yl)-amide (176 mg, 0.46 mmol) in methanol (6 ml), 4-fluoro-3-(trifluoromethyl) benzaldehyde (90 mg, 0.46 mmol) and sodium triacetoxyborohydride (293 mg, 1.38 mmol) at 25° C. The resulting solution was stirred at 25° C. overnight. At this time, the reaction mixture was treated with triethylamine (200 mL, 1.44 mmol) and then was stirred for an additional 24 h. At this time, the reaction was concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, gradient elution 95/5 methylene chloride/methanol) afforded 1-[2-(4-fluoro-3-trifluoromethyl-benzylamino)-ethyl]-3-(7-methoxy-thiazolo[5,4-d]pyrimidin-2-yl)-urea (37 mg, 18%); ES-HRMS m/e calcd for C17H16F4N6O2S (M+H)+ 445.1065, found 445.1065.

後処理

  1. customat 25° C
  2. stirringwas stirred for an additional 24 h
  3. concentrationAt this time, the reaction was concentrated in vacuo
  4. washFlash chromatography (Merck Silica gel 60, 230-400 mesh, gradient elution 95/5 methylene chloride/methanol)

出典と根拠

ORDレコード
ord-ba39de26c4c24720851a8cbd412f5c07
出典データセット
uspto-grants-2011_05
特許番号
US07947692B2

関連ノート

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