1,1,3,3-Tetramethylguanidine → HCID 53675923、化合物

HRID 1066524

反応式

HRID 1066524 の反応式
[CH3:1][O:2][C:3]1[C:8]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16][CH3:17])=[C:7]([NH:18][S:19]([C:22]2[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][N:23]=2)(=[O:21])=[O:20])[N:6]=[C:5]([C:29]2[CH:34]=[CH:33][N:32]=[C:31]([C:35]([OH:37])=[O:36])[CH:30]=2)[N:4]=1.CN(C)C(N(C)C)=N.Cl[CH:47]([O:49][C:50](=[O:52])[CH3:51])[CH3:48]>CN(C=O)C>[C:50]([O:49][CH:47]([O:36][C:35]([C:31]1[CH:30]=[C:29]([C:5]2[N:4]=[C:3]([O:2][CH3:1])[C:8]([O:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[O:16][CH3:17])=[C:7]([NH:18][S:19]([C:22]3[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][N:23]=3)(=[O:21])=[O:20])[N:6]=2)[CH:34]=[CH:33][N:32]=1)=[O:37])[CH3:48])(=[O:52])[CH3:51]

参加物

5

反応物 3

HCID 664601,1,3,3-TetramethylguanidineHCID 5218651-Chloroethyl acetateHCID 98929854-[4-Methoxy-5-(2-methoxy-phenoxy)-6-(5-methyl-pyridine-2-sulfonylamino)-pyrimidin-2-yl]-pyridine-2-carboxylic acid2 回

生成物 1

HCID 53675923HCID 53675923、化合物

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

To a solution of 0.52 g of 4-[4-methoxy-5-(2-methoxy-phenoxy)-6-(5-methyl-pyridine-2-sulfonylamino)-pyrimidin-2-yl]-pyridine-2-carboxylic acid, product of example 21, in DMF (10 ml) were added at RT 0.23 g of 1,1,3,3-tetramethylguanidine followed by 0,245 g of acetic acid 1-chloroethyl ester (preparation described by M. Ertan et al., Arzneim. Forsch. 1992, Vol. 42, 70). The reaction mixture was then heated at 60° C. for 20 h, cooled to RT and partitioned between ice water and EtOAc. The organic layer was washed with water, dried over Na2SO4 and the organic layer was removed in vacuo. The residue was purified on a silica gel chromatography column (eluted with tert-butyl methyl ether). Combinations of the purified fractions and evacuation in vacuo afforded 4-[4-methoxy-5-(2-methoxy-phenoxy)-6-(5-methyl-pyridine-2-sulfonylamino)-pyrimidin-2-yl]-pyridine-2-carboxylic acid 1-acetoxy-ethyl ester as a white solid. ISN mass spectrum, m/e 608 (M−1 calculated for C28H27N5O9S: 608).

後処理

  1. temperaturecooled to RT
  2. custompartitioned between ice water and EtOAc
  3. washThe organic layer was washed with water
  4. dry with materialdried over Na2SO4
  5. customthe organic layer was removed in vacuo
  6. customThe residue was purified on a silica gel chromatography column (eluted with tert-butyl methyl ether)

出典と根拠

ORDレコード
ord-662a365c4ffa4922b718df7d3082241d
出典データセット
uspto-grants-2001_06
特許番号
US06242601B1

関連ノート

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