1,2-Dichloroethane → methyl 4-[[1-[4-[N'-(2-fluorophenyl)ureido]-3-methoxyphenylacetyl]methylamino]-2-methyl-2-propoxy]benzoate

HRID 354494ノート

反応式

HRID 354494 の反応式
[CH3:1][NH:2][CH2:3][C:4]([CH3:17])([O:6][C:7]1[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][CH:8]=1)[CH3:5].[F:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[NH:25][C:26](=[O:40])[NH:27][C:28]1[CH:33]=[CH:32][C:31]([CH2:34][C:35](O)=[O:36])=[CH:30][C:29]=1[O:38][CH3:39].C(Cl)CCl.O>CN(C1C=CN=CC=1)C.CN(C=O)C>[F:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[NH:25][C:26](=[O:40])[NH:27][C:28]1[CH:33]=[CH:32][C:31]([CH2:34][C:35]([CH2:1][NH:2][CH2:3][C:4]([CH3:17])([O:6][C:7]2[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][CH:8]=2)[CH3:5])=[O:36])=[CH:30][C:29]=1[O:38][CH3:39]

参加物

7

反応物 4

HCID 111,2-DichloroethaneHCID 962WaterHCID 23511825HCID 23511825、化合物HCID 69333050Methyl 4-(1-methylamino-2-methyl-2-propoxy)benzoate

生成物 1

HCID 69334761methyl 4-[[1-[4-[N'-(2-fluorophenyl)ureido]-3-methoxyphenylacetyl]methylamino]-2-methyl-2-propoxy]benzoate収率 44.3%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6228Dimethylformamide溶媒

実験手順

To a stirred mixture of methyl 4-(1-methylamino-2-methyl-2-propoxy)benzoate (200 mg, 0.84 mmol), 4-[N′-(2-fluorophenyl)ureido]-3-methoxyphenylacetic acid (268 mg, 0.84 mmol), 4-DMAP (125 mg, 1.0 mmol) in DMF (5 mL) was added EDC (220 mg, 1.14 mmol) at ambient temp. The resulting mixture was stirred for a further 10 hr at ambient temp. The mixture was poured into water, and extracted with EtOAc. The extract was washed with brine, dried over Na2SO4, and evaporated. The residual gum was triturated with CH2Cl2 and Et2O to give 200 mg (44.1%) methyl 4-[[1-[4-[N′-(2-fluorophenyl)ureido]-3-methoxyphenylacetyl]methylamino]-2-methyl-2-propoxy]benzoate as a crystalline material. 1H-NMR (CDCl3) δ1.36 and 1.31 (each s, 6H), 3.24-3.88 (series of s, 13 H), 6.65-8.20 (series of m, 14H).

後処理

  1. extractionextracted with EtOAc
  2. washThe extract was washed with brine
  3. dry with materialdried over Na2SO4
  4. customevaporated
  5. customThe residual gum was triturated with CH2Cl2 and Et2O

出典と根拠

ORDレコード
ord-a2935f98208d4f0290ee014926308275
出典データセット
uspto-grants-2004_06
特許番号
US06756378B2

反応ノート

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