Ammonium formate → N-cyclopropyl-3-(3-(1-(2-hydroxyphenyl)cyclobutylamino)-2-oxopyrazin-1(2H)-yl)-4-methylbenzamide

HRID 337106ノート

反応式

HRID 337106 の反応式
C([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1([NH:19][C:20]2[C:21](=[O:40])[N:22]([C:27]3[CH:28]=[C:29]([CH:36]=[CH:37][C:38]=3[CH3:39])[C:30]([NH:32][CH:33]3[CH2:35][CH2:34]3)=[O:31])[CH:23]=[C:24](Br)[N:25]=2)[CH2:18][CH2:17][CH2:16]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>C(O)C.[Pd]>[CH:33]1([NH:32][C:30](=[O:31])[C:29]2[CH:36]=[CH:37][C:38]([CH3:39])=[C:27]([N:22]3[CH:23]=[CH:24][N:25]=[C:20]([NH:19][C:15]4([C:10]5[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=5[OH:8])[CH2:18][CH2:17][CH2:16]4)[C:21]3=[O:40])[CH:28]=2)[CH2:34][CH2:35]1

参加物

5

反応物 2

HCID 2723923Ammonium formateHCID 666896093-(3-(1-(2-(benzyloxy)phenyl)cyclobutylamino)-5-bromo-2-oxopyrazin-1(2H)-yl)-N-cyclopropyl-4-methylbenzamide

生成物 1

HCID 66688790N-cyclopropyl-3-(3-(1-(2-hydroxyphenyl)cyclobutylamino)-2-oxopyrazin-1(2H)-yl)-4-methylbenzamide収率 79.2%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

反応条件

温度
75 °C

実験手順

To 3-(3-(1-(2-(benzyloxy)phenyl)cyclobutylamino)-5-bromo-2-oxopyrazin-1(2H)-yl)-N-cyclopropyl-4-methylbenzamide (Example 268e, 1.537 g) in ethanol (16 mL) was added ammonium formate (2.263 g) and 5% Pd/C (0.546 g) and the reaction heated at 75° C. for 1 h. The mixture was filtered through celite and the solid washed through with ethanol and dichloromethane. The filtrate was collected and the volatiles removed in vacuo. The residue was purified (SiO2 chromatography eluting with 0-30% diethyl ether in dichloromethane) to afford the subtitle product (0.874 g).

後処理

  1. filtrationThe mixture was filtered through celite
  2. washthe solid washed through with ethanol and dichloromethane
  3. customThe filtrate was collected
  4. customthe volatiles removed in vacuo
  5. customThe residue was purified
  6. wash(SiO2 chromatography eluting with 0-30% diethyl ether in dichloromethane)

出典と根拠

ORDレコード
ord-1b1bc2c2b4d849678d7896cef3e65f4a
出典データセット
uspto-grants-2014_11
特許番号
US08889692B2

反応ノート

読み込み中…