3,4-Dichlorobenzaldehyde → 3-Phenylpropyl 4-(3,4-dichlorophenyl)-6-[(2-(1-piperidinyl)ethoxy)methyl]-2-(2-thienyl)-1,4-dihydropyrimidine-5-carboxylate

HRID 324776

反応式

HRID 324776 の反応式
[N:1]1([CH2:7][CH2:8][O:9][CH2:10][C:11](=O)[CH2:12][C:13]([O:15][CH2:16][CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:14])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:26][C:27]1[CH:28]=[C:29]([CH:32]=[CH:33][C:34]=1[Cl:35])[CH:30]=O.Cl.[C:37]([C:40]1[S:41][CH:42]=[CH:43][CH:44]=1)(=[NH:39])[NH2:38].C(=O)([O-])O.[Na+]>CN(C)C=O>[Cl:26][C:27]1[CH:28]=[C:29]([CH:30]2[C:12]([C:13]([O:15][CH2:16][CH2:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[O:14])=[C:11]([CH2:10][O:9][CH2:8][CH2:7][N:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)[NH:39][C:37]([C:40]3[S:41][CH:42]=[CH:43][CH:44]=3)=[N:38]2)[CH:32]=[CH:33][C:34]=1[Cl:35]

参加物

6

反応物 4

HCID 227103,4-DichlorobenzaldehydeHCID 516892Sodium BicarbonateHCID 2781759Thiophene-2-carboximidamide HydrochlorideHCID 220055123-Phenylpropyl 4-(2-(1-piperidinyl)ethoxy)acetoacetate

生成物 1

HCID 220055453-Phenylpropyl 4-(3,4-dichlorophenyl)-6-[(2-(1-piperidinyl)ethoxy)methyl]-2-(2-thienyl)-1,4-dihydropyrimidine-5-carboxylate収率 15.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

A mixture of 3-phenylpropyl 4-(2-(1-piperidinyl)ethoxy)acetoacetate (2.7 g, 7.77 mmol), 3,4-dichlorobenzaldehyde (1.63 g, 9.32 mmol), 2-amidinothiophene hydrochloride (1.52 g, 9.32 mmol) and sodium hydrogen carbonate (0.79 g, 9.35 mmol) was stirred in N,N-dimethylformamide (20 mL) for 4 days at room temperature and then heated to 60° C. for 3 days. The DMF was removed in vacuo and ethyl acetate was added to the residue. The precipitate was removed by filtration and the filtrate was washed with water, sodium hydrogen carbonate solution and brine, dried and evaporated to yield an oil. The oil was further purified by flash chromatography and RP-HPLC to give the title compound (0.73 g) as an oil. Electrospray MS m/z 612/614 [M+H]+.

後処理

  1. customThe DMF was removed in vacuo and ethyl acetate
  2. additionwas added to the residue
  3. customThe precipitate was removed by filtration
  4. washthe filtrate was washed with water, sodium hydrogen carbonate solution and brine
  5. customdried
  6. customevaporated
  7. customto yield an oil
  8. customThe oil was further purified by flash chromatography and RP-HPLC

出典と根拠

ORDレコード
ord-a9bd8567d7cd499ba949c25d9a9a3cba
出典データセット
uspto-grants-2001_04
特許番号
US06218538B1

関連ノート

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