Triethylamine → 1-{2-Oxo-2-[4-(4-pyrimidin-2-yl-phenyl)-piperazin-1-yl]-ethyl}-pyrrolidine-3-carboxylic acid methyl ester

HRID 1037984ノート

反応式

HRID 1037984 の反応式
[N:1]1([C:7]2[CH:12]=[CH:11][C:10]([C:13]3[N:18]=[CH:17][CH:16]=[CH:15][N:14]=3)=[CH:9][CH:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[CH3:19][O:20][C:21]([CH:23]1[CH2:27][CH2:26][N:25]([CH2:28][C:29](O)=[O:30])[CH2:24]1)=[O:22].C(N(CC)CC)C.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>CN(C=O)C>[CH3:19][O:20][C:21]([CH:23]1[CH2:27][CH2:26][N:25]([CH2:28][C:29](=[O:30])[N:4]2[CH2:5][CH2:6][N:1]([C:7]3[CH:12]=[CH:11][C:10]([C:13]4[N:14]=[CH:15][CH:16]=[CH:17][N:18]=4)=[CH:9][CH:8]=3)[CH2:2][CH2:3]2)[CH2:24]1)=[O:22]

参加物

7

反応物 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 534203192-(4-(Piperazin-1-yl)phenyl)pyrimidine2 回HCID 674208411-Carboxymethyl-pyrrolidine-3-carboxylic acid methyl ester2 回

生成物 1

HCID 674190531-{2-Oxo-2-[4-(4-pyrimidin-2-yl-phenyl)-piperazin-1-yl]-ethyl}-pyrrolidine-3-carboxylic acid methyl ester収率 83.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

2-(4-piperazin-1-yl-phenyl)-pyrimidine (compound 10 from Step 7, 14.7 mmol) and 1-Carboxymethyl-pyrrolidine-3-carboxylic acid methyl ester (compound 5 from Step 3, 17.6 mmol) were dissolved in 72 ml of DMF. Triethylamine (8 ml, 57 mmol), 1-hydroxybenztriazole (2.29 gm) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCl) (3.43 gm, 18 mmol) were added and the reaction mixture stirred for 24 hrs. After washing with brine, extracting with dichloromethane, and drying over magnesium sulfate, the mixture was evaporated and chromatographed on silica gel to obtain 5.0 gm of title product.

後処理

  1. washAfter washing with brine
  2. extractionextracting with dichloromethane
  3. dry with materialdrying over magnesium sulfate
  4. customthe mixture was evaporated
  5. customchromatographed on silica gel

出典と根拠

ORDレコード
ord-f500272d170e45e2b7ea02e06a48716c
出典データセット
uspto-grants-2013_10
特許番号
US08546404B2

反応ノート

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