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 (R)-1-methylbutyl ester

HRID 2089650

反応式

HRID 2089650 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+].[CH3:50][C@@H:51]([O:55][C:56](=[O:61])[O:57][CH:58](Cl)[CH3:59])[CH2:52][CH2:53][CH3:54]>CN(C=O)C>[CH3:50][C@@H:51]([O:55][C:56](=[O:61])[O:57][CH:58]([O:16][C:14]1[N:13]([C:17]2[N:18]=[CH:19][CH:20]=[CH:21][N:22]=2)[N:12]=[C:11]([CH:10]([NH:9][C:6]2[CH:7]=[CH:8][C:3]([C:2]([NH2:1])=[N:36][C:37](=[O:44])[C:38]3[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=3)=[CH:4][CH:5]=2)[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])[N:15]=1)[CH3:59])[CH2:52][CH2:53][CH3:54]

参加物

5

反応物 3

HCID 516893Potassium BicarbonateHCID 86677396Carbonic acid 1-chloroethyl ester (R)-1-methylbutyl esterHCID 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 68212851Carbonic 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 (R)-1-methylbutyl ester収率 68.6%

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, 150 mg) and DMF (3 mL), potassium hydrogen carbonate (150 mg) and carbonic acid 1-chloroethyl ester (R)-1-methylbutyl ester (150 mg) were sequentially added, and the resulting mixture was stirred at 55° C. for 18 hours. The reaction mixture was purified by reverse phase silica gel column chromatography (mixed solvent of acetonitrile-water) to obtain the captioned compound (130 mg).

後処理

  1. additionwere sequentially added
  2. customThe reaction mixture was purified by reverse phase silica gel column chromatography (mixed solvent of acetonitrile-water)

出典と根拠

ORDレコード
ord-cd80c84de7414ed098101f318cf47ce2
出典データセット
uspto-grants-2013_05
特許番号
US08436009B2

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