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

반응식

HRID 423369 반응식
[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]

참가 물질

6

반응물 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 180705825-Chloro-6-isopropoxynicotinic acidHCID 178471833HCID 178471833, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

반응 조건

온도
80 °C

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-6f9cec4545a74e8c8c10ac344dbdde35
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08101775B2

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