1-Hydroxybenzotriazole → HCID 57917670、化合物

HRID 1878411ノート

反応式

HRID 1878411 の反応式
[C:1]1([NH:7][C:8](=[O:21])[NH:9][C:10]2[CH:20]=[CH:19][C:13]([C:14]([O:16]CC)=O)=[CH:12][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.FC(F)(F)C(O)=O.FC(F)(F)C(O)=O.[N:36]1([CH2:42][C:43]2[CH:44]=[C:45]([CH:50]=[CH:51][CH:52]=2)[C:46]([O:48][CH3:49])=[O:47])[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]1.C(N(C(C)C)C(C)C)C.N1(O)C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>CN(C)C=O>[C:1]1([NH:7][C:8](=[O:21])[NH:9][C:10]2[CH:11]=[CH:12][C:13]([C:14]([N:39]3[CH2:38][CH2:37][N:36]([CH2:42][C:43]4[CH:44]=[C:45]([CH:50]=[CH:51][CH:52]=4)[C:46]([O:48][CH3:49])=[O:47])[CH2:41][CH2:40]3)=[O:16])=[CH:19][CH:20]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

参加物

7

反応物 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2768344ethyl 4-(3-phenylureido)benzoateHCID 86635135HCID 86635135、化合物

生成物 1

HCID 57917670HCID 57917670、化合物収率 79.9%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of ethyl 4-(3-phenylureido)benzoate (1.00 g, 3.90 mmol) in N,N-dimethylform-amide (20 mL) was added methyl 3-(piperazin-1-ylmethyl)benzoate bis(2,2,2-trifluoroacetate) (1.25 g, 2.70 mmol), N-ethyl-N-isopropylpropan-2-amine (0.94 mL, 5.40 mmol), 1H-benzo[d][1,2,3]triazol-1-ol (0.40 g, 2.97 mmol, HOBT) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.57 g, 2,97 mmol, EDCl). The mixture was stirred overnight at room temperature and then concentrated under vacuum. The residue was taken up in ethyl acetate and washed with water (×2) and then saturated aqueous sodium chloride. The organic phase was dried on magnesium sulfate, filtered, concentrated under vacuum. Silica chromatography (10-40% ethyl acetate in n-hexanes) and recrystallisation from methanol gave the title compound (1.02 g).

後処理

  1. concentrationconcentrated under vacuum
  2. washwashed with water (×2)
  3. customThe organic phase was dried on magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customSilica chromatography (10-40% ethyl acetate in n-hexanes) and recrystallisation from methanol

出典と根拠

ORDレコード
ord-8faaa3e0acb54b40813c45d2e35b9aac
出典データセット
uspto-grants-2012_11
特許番号
US08314091B2

反応ノート

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