[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 337077ノート

反応式

HRID 337077 の反応式
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]

参加物

4

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-6daa0b32a98b46fdbb38cb5e880c8bef
出典データセット
uspto-grants-2014_11
特許番号
US08889692B2

反応ノート

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