Dimethylformamide → HCID 178502388、化合物

HRID 1776048ノート

反応式

HRID 1776048 の反応式
[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]

参加物

9

反応物 7

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

生成物 1

HCID 178502388HCID 178502388、化合物

試薬・触媒・溶媒 1

HCID 313Hydrochloric Acid溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-8b028c0c7f204187b409f12c32b2e044
出典データセット
uspto-grants-2016_02
特許番号
US09260414B2

反応ノート

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