Dimethylformamide → HCID 178502388, 화합물

HRID 1411366노트

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HRID 1411366 반응식
[C:1](Cl)(=[O:5])[C:2](Cl)=O.C(OC([N:14]1[CH2:19][CH2:18][N:17]([C:20]2[CH:25]=[CH:24]C(C(O)=O)=[CH:22][N:21]=2)[CH2:16][CH2:15]1)=O)(C)(C)C.ClCCl.CN(C)C=O.C(N(CC)C(C)C)(C)C.[CH3:46][O:47][C:48](=[O:79])[NH:49][C@H:50]([C:54]([N:56]1[CH2:60][CH2:59][CH2:58][C@H:57]1[C:61]1[NH:62][CH:63]=[C:64]([C:66]2[CH:71]=[CH:70][C:69]([C:72]3[CH:77]=[CH:76][C:75]([NH2:78])=[CH:74][CH:73]=3)=[CH:68][CH:67]=2)[N:65]=1)=[O:55])[CH:51]([CH3:53])[CH3:52].O1CCOCC1>Cl>[CH3:46][O:47][C:48](=[O:79])[NH:49][C@H:50]([C:54]([N:56]1[CH2:60][CH2:59][CH2:58][C@H:57]1[C:61]1[NH:62][CH:63]=[C:64]([C:66]2[CH:67]=[CH:68][C:69]([C:72]3[CH:73]=[CH:74][C:75]([NH:78][C:1]([C:2]4[CH:22]=[N:21][C:20]([N:17]5[CH2:16][CH2:15][NH:14][CH2:19][CH2:18]5)=[CH:25][CH:24]=4)=[O:5])=[CH:76][CH:77]=3)=[CH:70][CH:71]=2)[N:65]=1)=[O:55])[CH:51]([CH3:53])[CH3:52]

참가 물질

9

반응물 7

HCID 6228DimethylformamideHCID 6344DichloromethaneHCID 312751,4-DioxaneHCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 27718236-(4-((Tert-butoxy)carbonyl)piperazin-1-yl)pyridine-3-carboxylic acidHCID 178502377HCID 178502377, 화합물

생성물 1

HCID 178502388HCID 178502388, 화합물

시약·촉매·용매 1

HCID 313Hydrochloric Acid용매

실험 절차

Oxalyl chloride (44.0 uL, 0.520 mmol) was added to a solution of 4-(5-carboxy-pyridin-2-yl)-piperazine-1-carboxylic acid tert-butyl ester (70.3 mg, 0.229 mmol) in dichloromethane (6.67 mL, 104 mmol) and N,N-dimethylformamide (2.01 uL, 0.026 mmol) The reaction mixture was stirred at room temperature for 20 min and then N,N-diisopropylethylamine (0.181 mL, 1.04 mmol) was added followed by ((S)-1-{(S)-2-[4-(4′-amino-biphenyl-4-yl)-1H-imidazol-2-yl]-pyrrolidine-1-carbonyl}-2-methyl-propyl)-carbamic acid methyl ester (100.0 mg, 0.217 mmol). The reaction mixture was stirred for 2 h at room temperature, then dried by rotary evaporation. The crude material was dissolved in dichloromethane (1 mL) and then washed with saturated aqueous sodium bicarbonate (1 mL). The organic layer was concentrated, dissolved in 4.0 M hydrogen chloride in 1,4-dioxane (6.7 mL, 27 mmol) and stirred for 1 h at room temperature until completely deprotected. The reaction mixture was concentrated and used directly in the next step.

후처리

  1. stirringThe reaction mixture was stirred for 2 h at room temperature
  2. customdried by rotary evaporation
  3. dissolutionThe crude material was dissolved in dichloromethane (1 mL)
  4. washwashed with saturated aqueous sodium bicarbonate (1 mL)
  5. concentrationThe organic layer was concentrated
  6. stirringstirred for 1 h at room temperature
  7. concentrationThe reaction mixture was concentrated

출처 및 근거

ORD 기록
ord-096b887c47cd46a49ba9edbd2db2d89f
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08921372B2

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