Potassium Bicarbonate → Carbonic acid 1-(5-{(4-{amino[benzoylimino]methyl}phenylamino)-[2-fluoro-3-(2-hydroxyethoxy)-5-methoxyphenyl]methyl}-2-pyrimidin-2-yl-2H-[1,2,4]triazol-3-yloxy)ethyl ester cyclohexyl ester

HRID 2089629

反応式

HRID 2089629 の反応式
[NH2:1][C:2](=[N:36][C:37](=[O:44])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C:3]1[CH:8]=[CH:7][C:6]([NH:9][CH:10]([C:23]2[CH:28]=[C:27]([O:29][CH3:30])[CH:26]=[C:25]([O:31][CH2:32][CH2:33][OH:34])[C:24]=2[F:35])[C:11]2[NH:15][C:14](=[O:16])[N:13]([C:17]3[N:22]=[CH:21][CH:20]=[CH:19][N:18]=3)[N:12]=2)=[CH:5][CH:4]=1.C(=O)([O-])O.[K+].[C:50](=[O:62])([O:55][CH:56]1[CH2:61][CH2:60][CH2:59][CH2:58][CH2:57]1)[O:51][CH:52](Cl)[CH3:53]>CN(C=O)C>[CH:56]1([O:55][C:50](=[O:62])[O:51][CH:52]([O:16][C:14]2[N:13]([C:17]3[N:18]=[CH:19][CH:20]=[CH:21][N:22]=3)[N:12]=[C:11]([CH:10]([NH:9][C:6]3[CH:7]=[CH:8][C:3]([C:2]([NH2:1])=[N:36][C:37](=[O:44])[C:38]4[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=4)=[CH:4][CH:5]=3)[C:23]3[CH:28]=[C:27]([O:29][CH3:30])[CH:26]=[C:25]([O:31][CH2:32][CH2:33][OH:34])[C:24]=3[F:35])[N:15]=2)[CH3:53])[CH2:61][CH2:60][CH2:59][CH2:58][CH2:57]1

参加物

5

反応物 3

HCID 516893Potassium BicarbonateHCID 112295291-Chloroethyl Cyclohexyl CarbonateHCID 136334022N-[1-amino-1-(4-{[[2-fluoro-3-(2-hydroxyethoxy)-5-methoxyphenyl]-(5-oxo-1-pyrimidin-2-yl-4,5-dihydro-1H-[1,2,4]triazol-3-yl)methyl]amino}phenyl)methylidene]benzamide

生成物 1

HCID 67471168Carbonic acid 1-(5-{(4-{amino[benzoylimino]methyl}phenylamino)-[2-fluoro-3-(2-hydroxyethoxy)-5-methoxyphenyl]methyl}-2-pyrimidin-2-yl-2H-[1,2,4]triazol-3-yloxy)ethyl ester cyclohexyl ester収率 52.9%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
55 °C

実験手順

To a mixture of N-[1-amino-1-(4-{[[2-fluoro-3-(2-hydroxyethoxy)-5-methoxyphenyl]-(5-oxo-1-pyrimidin-2-yl-4,5-dihydro-1H-[1,2,4]triazol-3-yl)methyl]amino}phenyl)methylidene]benzamide (Example 1a, 1.0 g) and DMF (20 mL), potassium hydrogen carbonate (1.67 g) and 1-chloroethyl cyclohexyl carbonate (2.76 g) were added, and the resulting mixture was stirred at 55° C. for 26 hours. The reaction solution was filtered, and the filtrate obtained was concentrated under reduced pressure. The residue obtained was purified by NAM silica gel column chromatography (mixed solvent of methanol-ethyl acetate) to obtain the captioned compound (680 mg).

後処理

  1. additionwere added
  2. filtrationThe reaction solution was filtered
  3. customthe filtrate obtained
  4. concentrationwas concentrated under reduced pressure
  5. customThe residue obtained
  6. customwas purified by NAM silica gel column chromatography (mixed solvent of methanol-ethyl acetate)

出典と根拠

ORDレコード
ord-2b6ad9cf33da400599b25bbc2a97d622
出典データセット
uspto-grants-2013_05
特許番号
US08436009B2

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