1-Hydroxybenzotriazole → HCID 57917670, 화합물

HRID 1878411노트

반응식

HRID 1878411 반응식
[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

참가 물질

7

반응물 5

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

생성물 1

HCID 57917670HCID 57917670, 화합물수율 79.9%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-8faaa3e0acb54b40813c45d2e35b9aac
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08314091B2

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