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

HRID 1697366노트

반응식

HRID 1697366 반응식
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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

반응 조건

온도
75 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-e6afeca0667b490a8e154a5b6ad3945d
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08163905B2

반응 노트

불러오는 중…