1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 3-[4-(5-{5-Chloro-6-[(1-methylethyl)oxy]-3-pyridinyl}-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl]propanoic acid

HRID 423369

反応式

HRID 423369 の反応式
[OH:1][NH:2][C:3](=[NH:20])[C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[CH:7][N:8]2[CH2:13][CH2:14][C:15]([O:17]CC)=[O:16].[Cl:21][C:22]1[CH:23]=[C:24]([C:32](O)=O)[CH:25]=[N:26][C:27]=1[O:28][CH:29]([CH3:31])[CH3:30].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>CN(C=O)C>[Cl:21][C:22]1[CH:23]=[C:24]([C:32]2[O:1][N:2]=[C:3]([C:4]3[CH:12]=[CH:11][CH:10]=[C:9]4[C:5]=3[CH:6]=[CH:7][N:8]4[CH2:13][CH2:14][C:15]([OH:17])=[O:16])[N:20]=2)[CH:25]=[N:26][C:27]=1[O:28][CH:29]([CH3:30])[CH3:31]

参加物

6

反応物 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 180705825-Chloro-6-isopropoxynicotinic acidHCID 178471833HCID 178471833、化合物

生成物 1

HCID 249867423-[4-(5-{5-Chloro-6-[(1-methylethyl)oxy]-3-pyridinyl}-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl]propanoic acid収率 20.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
80 °C

実験手順

Ethyl 3-{4-[(hydroxyamino)(imino)methyl]-1H-indol-1-yl}propanoate (D57) (150 mg) in DMF (2.5 ml) was added to a solution of 5-chloro-6-[(1-methylethyl)oxy]-3-pyridinecarboxylic acid (D61) (118 mg), HOBT (81 mg) and EDCI (114 mg) which had been stirring at RT for 10 minutes in DMF (2.5 ml). The resultant mixture was stirred at RT for 2 hours then heated at 80° C. for three days. The reaction mixture was evaporated to dryness and extracted from H2O (25 ml) with EtOAc (2×25 ml). The combined organics were evaporated and the residue stirred in EtOH/2 M aq. NaOH (1:1 mixture, 20 ml) at 50° C. for 2 hours. The EtOH was evaporated and the precipitate removed by filtration. This was acidified then purified by MDAP to give the title compound (48 mg) as an off white solid. δH (d6-DMSO, 400 MHz): 1.40 (6H, d), 2.80 (2H, t), 4.50 (2H, t), 5.46 (1H, septet), 7.08 (1H, d), 7.36 (1H, apparent t), 7.60 (1H, d), 7.82 (1H, d), 7.95 (1H, d), 8.60 (1H, d), 8.97 (1H, d). MS (ES−): C21H1935ClN4O4 requires 426; found 425 (M−H+).

後処理

  1. customThe reaction mixture was evaporated to dryness
  2. extractionextracted from H2O (25 ml) with EtOAc (2×25 ml)
  3. customThe combined organics were evaporated
  4. customThe EtOH was evaporated
  5. customthe precipitate removed by filtration
  6. customThis was acidified then purified by MDAP

出典と根拠

ORDレコード
ord-6f9cec4545a74e8c8c10ac344dbdde35
出典データセット
uspto-grants-2012_01
特許番号
US08101775B2

関連ノート

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