Diisopropylethylamine → HCID 178488472, 화합물

HRID 2102241노트

반응식

HRID 2102241 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[N:13]([CH2:14][C:15]3[CH:23]=[CH:22][C:18]([C:19]([OH:21])=O)=[CH:17][CH:16]=3)[N:12]=[C:11]([C:24]3[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=3)[CH:10]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.O[N:33]1[C:37]2[N:38]=CC=C[C:36]=2[N:35]=[N:34]1.C([N:45](CC)C(C)C)(C)C.Cl.CN(C)CCCN=C=NCC>C(OCC)(=O)C.CN(C=O)C.C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[N:13]([CH2:14][C:15]3[CH:23]=[CH:22][C:18]([C:19]([NH:38][CH2:37][C:36]4[NH:45][N:33]=[N:34][N:35]=4)=[O:21])=[CH:17][CH:16]=3)[N:12]=[C:11]([C:24]3[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=3)[CH:10]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

참가 물질

7

반응물 4

HCID 81531DiisopropylethylamineHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 67337219HCID 67337219, 화합물

생성물 1

HCID 178488472HCID 178488472, 화합물

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 22350042dichloromethane N,N-dimethylformamide용매

실험 절차

To a solution of the intermediate from example 76 step A (100 mg, 0.22 mmol) in 1:1 DMF/DCM (0.54 mL) was added 1-hydroxy-7-azabenzo-triazole (35 mg, 0.264 mmol), N,N-diisopropylethyl amine (92 μL, 0.53 mmol) amino methyl tetrazole (26 mg, 0.26 mmol) and 1-(3-(Dimethylamino)propyl-3-ethyl carbodiimide hydrochloride (51 mg, 0.26 mmol). The reaction was left stirring at room temperature for 18 hours. The reaction was diluted with ethyl acetate, washed with 1N HCl, dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by reverse phase HPLC (Gilson) to give the title compound. 1H NMR (DMSO, 500 MHz): δ 9.22(t, J=5.5 Hz, 1H), 7.84(d, J=8.5 Hz, 2H), 7.79(d, J=8.9 Hz, 2H), 7.69(t, J=1.9 Hz, 1H), 7.54(d, J=1.8 Hz, 2H), 7.17(d, J=8.2 Hz, 2H), 7.06(s, 1H), 7.0(d, J=8.7 Hz, 2H), 5.53(s, 2H), 4.74(d, J=5.5 Hz, 2H), 3.79(s, 3H). LC-MS: 2.32 min; (M+H)=534.3.

후처리

  1. waitThe reaction was left
  2. washwashed with 1N HCl
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by reverse phase HPLC (Gilson)

출처 및 근거

ORD 기록
ord-b9cc9d682bcf46ada1444126372cbbaa
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07572922B2

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