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

HRID 337106노트

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HRID 337106 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

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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-1b1bc2c2b4d849678d7896cef3e65f4a
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889692B2

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