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Diisopropylethylamine → 1-(4-Amino-quinazolin-7-ylmethyl)-4-(6-chloro-1H-benzimidazole-2-carbonyl)-3-(S)-methoxymethyl-piperazin-2-one

HRID 1432979
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HRID 1432979 반응식
C([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([CH2:17][C:18]2[CH:27]=[C:26]3[C:21]([C:22]([NH2:28])=[N:23][CH:24]=[N:25]3)=[CH:20][CH:19]=2)[C:13](=[O:29])[CH:12]1[CH2:30][O:31][CH3:32])=O)C1C=CC=CC=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(C(C)C)CC)(C)C.[Cl:64][C:65]1[CH:66]=[CH:67][C:68]2[N:72]=[C:71](C(O)=O)[NH:70][C:69]=2[CH:76]=1>CN(C=O)C>[NH2:28][C:22]1[C:21]2[C:26](=[CH:27][C:18]([CH2:17][N:14]3[CH2:15][CH2:16][N:11]([C:9]([C:71]4[NH:70][C:69]5[CH:76]=[C:65]([Cl:64])[CH:66]=[CH:67][C:68]=5[N:72]=4)=[O:8])[C@@H:12]([CH2:30][O:31][CH3:32])[C:13]3=[O:29])=[CH:19][CH:20]=2)[N:25]=[CH:24][N:23]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 105121106-Chloro-1H-benzimidazole-2-carboxylic acidHCID 54306307HCID 54306307, 화합물

생성물 1

HCID 545534321-(4-Amino-quinazolin-7-ylmethyl)-4-(6-chloro-1H-benzimidazole-2-carbonyl)-3-(S)-methoxymethyl-piperazin-2-one수율 55%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 4-(4-amino-quinazoline-7-ylmethyl)-2-methoxymethyl-3-oxo-piperazine-1-carboxylic acid benzyl ester, EXAMPLE 75, (20 mg, 0.066 mmol) in 1.5 mL of DMF is added TBTU (923.4 mg, 0.073 mmol), diisopropylethylamine (0.013 ml, 0.073 mmol) and 6-chloro-1H-benzoimidazole-2-carboxylic acid (prepared from literature in Eur.J.med.Chem. 1993, 28, 71) (14.3 mg, 0.073 mmol). The resulting mixture is left to stir at room temperature overnight. The crude mixture is directly purified by reverse phase HPLC (10-70% ACN/H2O). The product (30.1 mg, 55%) is isolated as a white powder. C23H22ClN7O3 MS m/z: 480, 481. Anal. cald. for C23H22ClN7O3. 2C2HF3O2: C, 45.81; H, 3.42; N, 13.85. Found C, 45.19; H, 3.59; N, 13.76.

후처리

  1. waitThe resulting mixture is left
  2. customThe crude mixture is directly purified by reverse phase HPLC (10-70% ACN/H2O)

출처 및 근거

ORD 기록
ord-670a80a47ee047bba5509b898019c11f
출처 데이터셋
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07612075B2

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