Diisopropylethylamine → HCID 178488473, 화합물

HRID 2102237노트

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HRID 2102237 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:13]=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)[N:11]([CH2:22][C:23]3[CH:31]=[CH:30][C:26]([C:27](O)=[O:28])=[CH:25][CH:24]=3)[N:10]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.O[N:33]1[C:37]2[N:38]=CC=CC=2[N:35]=[N:34]1.C([N:45](CC)C(C)C)(C)C.Cl.CN(C)CCCN=C=NCC.NC1NN=NN=1.F[P-](F)(F)(F)(F)F.Br[P+](N1CCCC1)(N1CCCC1)N1CCCC1>C(Cl)Cl.CN(C=O)C.C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:13]=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)[N:11]([CH2:22][C:23]3[CH:31]=[CH:30][C:26]([C:27]([NH:45][C:37]4[NH:38][N:35]=[N:34][N:33]=4)=[O:28])=[CH:25][CH:24]=3)[N:10]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

참가 물질

9

반응물 6

HCID 81531DiisopropylethylamineHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2733179PyBroPHCID 67335518HCID 67335518, 화합물HCID 178509299HCID 178509299, 화합물

생성물 1

HCID 178488473HCID 178488473, 화합물

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 22350042dichloromethane N,N-dimethylformamide용매

실험 절차

To a solution of the intermediate from step D (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 tetrazole (56 mg, 0.66 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 checked by LC-MS and was found to have not gone to completion. An additional equivalent of amino tetrazole was added followed by Bromo-tris-pyrrolidino-phosphonium hexafluorophosphate (51 mg, 0.11 mmol). The reaction was complete in 3 hours. It was diluted with DCM (10 mL) and 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 8.04(d, J=8.5 Hz, 2H), 7.89(d, J=2.1 Hz, 2H), 7.56(t, J=1.9 Hz, 1H), 7.41(d, J=8.7 Hz, 2H), 7.21(d, J=8.4 Hz, 2H), 7.14(s, 1H), 7.05(d, J=8.7 Hz, 2H), 5.53(s, 2H), 3.79(s, 3H). LC-MS: 2.53 min; (M+H)=520.2.

후처리

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

출처 및 근거

ORD 기록
ord-5f90e1a26faf478ea1cdf567f2bd677b
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07572922B2

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