[2-[2-[1-[[4-[5-[(Ethylamino)carbonyl]-2-methylphenyl]-3,4-dihydro-3-oxopyrazinyl]amino]-1-methylethyl]phenoxy]ethyl]methyl-carbamic acid phenylmethyl ester → N-Ethyl-4-methyl-3-[3-[[1-methyl-1-[2-[2-(methylamino)ethoxy]phenyl]ethyl]amino]-2-oxo-1(2H)-pyrazinyl]-benzamide

HRID 337077노트

반응식

HRID 337077 반응식
C1(CO[C:9](=O)[N:10]([CH2:12][CH2:13][O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[C:21]([NH:24][C:25]2[C:30](=[O:31])[N:29]([C:32]3[CH:37]=[C:36]([C:38]([NH:40][CH2:41][CH3:42])=[O:39])[CH:35]=[CH:34][C:33]=3[CH3:43])[CH:28]=[CH:27][N:26]=2)([CH3:23])[CH3:22])C)C=CC=CC=1>[Pd].C(O)C>[CH2:41]([NH:40][C:38](=[O:39])[C:36]1[CH:35]=[CH:34][C:33]([CH3:43])=[C:32]([N:29]2[CH:28]=[CH:27][N:26]=[C:25]([NH:24][C:21]([CH3:22])([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[O:14][CH2:13][CH2:12][NH:10][CH3:9])[CH3:23])[C:30]2=[O:31])[CH:37]=1)[CH3:42]

참가 물질

4

반응물 1

HCID 66689896[2-[2-[1-[[4-[5-[(Ethylamino)carbonyl]-2-methylphenyl]-3,4-dihydro-3-oxopyrazinyl]amino]-1-methylethyl]phenoxy]ethyl]methyl-carbamic acid phenylmethyl ester

생성물 1

HCID 66690353N-Ethyl-4-methyl-3-[3-[[1-methyl-1-[2-[2-(methylamino)ethoxy]phenyl]ethyl]amino]-2-oxo-1(2H)-pyrazinyl]-benzamide수율 0.2%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

실험 절차

To [2-[2-[1-[[4-[5-[(ethylamino)carbonyl]-2-methylphenyl]-3,4-dihydro-3-oxopyrazinyl]amino]-1-methylethyl]phenoxy]ethyl]methyl-carbamic acid phenylmethyl ester (Example 220d, 1.10 g) was added ethanol (10 mL) and this was pumped through a Pd/C cartridge at 1 mL/min under max H2 at 50° C. on an H-Cube hydrogenator. The solvents were removed in vacuo and the residue then taken up in acetonitrile. Purification by preparative HPLC (ACE column, 0.2% TFA:acetonitrile eluent) followed by treatment with SCX resin (eluting with methanol (discarded) followed by 7N NH3 in methanol and collected the basic fractions) and trituration with diethyl ether afforded the title product (2 mg).

후처리

  1. customThe solvents were removed in vacuo
  2. customPurification by preparative HPLC (ACE column, 0.2% TFA:acetonitrile eluent)
  3. washeluting with methanol (discarded)
  4. customcollected the basic fractions) and trituration with diethyl ether

출처 및 근거

ORD 기록
ord-6daa0b32a98b46fdbb38cb5e880c8bef
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889692B2

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