Propylphosphonic anhydride → 1-Methyl-4-(2-phenyl-imidazo[1,2-a]pyrimidin-7-ylcarbamoyl)-1H-pyrazole-3-carboxylic acid ethyl ester

HRID 1958333

反応式

HRID 1958333 の反応式
CCCP1(OP(CCC)(=O)OP(CCC)(=O)O1)=O.[C:19]1([C:25]2[N:26]=[C:27]3[N:32]=[C:31]([NH2:33])[CH:30]=[CH:29][N:28]3[CH:34]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[CH2:35]([O:37][C:38]([C:40]1[C:44]([C:45](O)=[O:46])=[CH:43][N:42]([CH3:48])[N:41]=1)=[O:39])[CH3:36].C(C(N(C(C)C)C(C)C)C)C>C(OCC)(=O)C>[CH2:35]([O:37][C:38]([C:40]1[C:44]([C:45](=[O:46])[NH:33][C:31]2[CH:30]=[CH:29][N:28]3[CH:34]=[C:25]([C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=4)[N:26]=[C:27]3[N:32]=2)=[CH:43][N:42]([CH3:48])[N:41]=1)=[O:39])[CH3:36]

参加物

6

反応物 4

HCID 111923Propylphosphonic anhydrideHCID 18997630EthyldiisopropylethylamineHCID 456006963-(ethoxycarbonyl)-1-methyl-1H-pyrazole-4-carboxylic acidHCID 508783902-Phenylimidazo[1,2-A]pyrimidin-7-amine

生成物 1

HCID 673923291-Methyl-4-(2-phenyl-imidazo[1,2-a]pyrimidin-7-ylcarbamoyl)-1H-pyrazole-3-carboxylic acid ethyl ester収率 29.7%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒2 回

反応条件

温度
0 °C

実験手順

At 0° C., propylphosphonic acid anhydride (1-propanephosphonic acid cyclic anhydride, 50% in ethyl acetate, 7.4 ml, 2.5 eq.) was added slowly to a solution of 2-phenylimidazo[1,2-a]pyrimidin-7-amine (example 1, step 1, 1.27 g, 6 mmol), 1-methyl-1H-pyrazole-3,4-dicarboxylic acid 3-ethyl ester (1.00 g, 5 mmol), and ethyldiisopropylethylamine (2.0 ml, 15 mmol) in ethyl acetate (20 ml). The mixture was stirred for 30 min at 0° C., and subsequently at RT for 48 h. The mixture was taken up in ethyl acetate, and washed with water. The combined water layers were adjusted to pH=9 (NaOH), and extracted with dichloromethane. All organic layers were combined, dried (Na2SO4), and evaporated. The title compound (580 mg, 29%) was obtained from the residue by column chromatography (silica gel, heptane:ethyl acetate=100:0-80:20). (1-Methyl-1H-pyrazole-3,4-dicarboxylic acid 3-ethyl ester was obtained by the method of Pérez et al., Spanish patent appl. ES 493459.)

後処理

  1. waitsubsequently at RT for 48 h
  2. washwashed with water
  3. extractionextracted with dichloromethane
  4. dry with materialdried (Na2SO4)
  5. customevaporated

出典と根拠

ORDレコード
ord-a10c765232c14f5096b2de306d39ef4b
出典データセット
uspto-grants-2013_04
特許番号
US08410117B2

関連ノート

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