1-Hydroxybenzotriazole → (2E)-3-(4-Chlorophenyl)-N-[(1S)-2-[(2-{4-[(3,5-dichloro-2-pyridyl)oxy]-1-piperidinyl}-2-oxoethyl)amino]-2-oxo-1-(2-pyridylmethyl)ethyl]-2-propenamide

HRID 1246756

反応式

HRID 1246756 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([NH:12][C@@H:13]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=2)[C:14]([NH:16][CH2:17][C:18]([OH:20])=O)=[O:15])=[O:11])=[CH:4][CH:3]=1.Cl.Cl.[Cl:30][C:31]1[C:32]([O:38][CH:39]2[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]2)=[N:33][CH:34]=[C:35]([Cl:37])[CH:36]=1.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.C(N(CC)C(C)C)(C)C>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5](/[CH:8]=[CH:9]/[C:10]([NH:12][C@@H:13]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=2)[C:14]([NH:16][CH2:17][C:18]([N:42]2[CH2:43][CH2:44][CH:39]([O:38][C:32]3[C:31]([Cl:30])=[CH:36][C:35]([Cl:37])=[CH:34][N:33]=3)[CH2:40][CH2:41]2)=[O:20])=[O:15])=[O:11])=[CH:6][CH:7]=1

参加物

7

反応物 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 219060913,5-Dichloro-2-(4-piperidinyloxy)pyridine dihydrochlorideHCID 69379045[[(2S)-2-[[(2E)-3-(4-Chlorophenyl)-2-propenoyl]amino]-3-(2-pyridyl)propanoyl]amino]acetic acid

生成物 1

HCID 69379614(2E)-3-(4-Chlorophenyl)-N-[(1S)-2-[(2-{4-[(3,5-dichloro-2-pyridyl)oxy]-1-piperidinyl}-2-oxoethyl)amino]-2-oxo-1-(2-pyridylmethyl)ethyl]-2-propenamide収率 76.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a mixture of {[(2S)-2-{[(2E)-3-(4-chlorophenyl)-2-propenoyl]amino}-3-(2-pyridyl)propanoyl]amino}acetic acid (0.19 g), 3,5-dichloro-2-(4-piperidinyloxy)pyridine dihydrochloride (0.16 g), 1-hydroxybenzotriazole (0.084 g) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.11 g) in N,N-dimethylformamide (2.5 ml) was added dropwise N,N-diisopropylethylamine (0.27 ml) at 8° C. The mixture was warmed to room temperature and stirred for 6 hours. The reaction mixture was poured into ice-water and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogencarbonate solution and brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography to give the title compound (231 mg).

後処理

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated aqueous sodium hydrogencarbonate solution and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-ea858edac1a64b4083b1cfca2779459a
出典データセット
uspto-grants-2006_10
特許番号
US07129243B2

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