Diisopropylethylamine → N1-(4-fluoro-3-(2-oxo-2-(4-(1-phenyl-1H-tetrazol-5-yl)piperazin-1-yl)acetyl)-1H-pyrrolo[2,3-c]pyridin-7-yl)-N2,N2-dimethyloxalamide

HRID 1157292ノート

反応式

HRID 1157292 の反応式
[NH2:1][C:2]1[N:3]=[CH:4][C:5]([F:32])=[C:6]2[C:10]([C:11](=[O:31])[C:12]([N:14]3[CH2:19][CH2:18][N:17]([C:20]4[N:24]([C:25]5[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=5)[N:23]=[N:22][N:21]=4)[CH2:16][CH2:15]3)=[O:13])=[CH:9][NH:8][C:7]=12.[CH3:33][N:34]([CH3:40])[C:35](=[O:39])[C:36](O)=[O:37].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C>[F:32][C:5]1[CH:4]=[N:3][C:2]([NH:1][C:36](=[O:37])[C:35]([N:34]([CH3:40])[CH3:33])=[O:39])=[C:7]2[NH:8][CH:9]=[C:10]([C:11](=[O:31])[C:12](=[O:13])[N:14]3[CH2:15][CH2:16][N:17]([C:20]4[N:24]([C:25]5[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=5)[N:23]=[N:22][N:21]=4)[CH2:18][CH2:19]3)[C:6]=12

参加物

6

反応物 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 2760995N,N-Dimethyloxamic acidHCID 248752521-(7-amino-4-fluoro-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-[4-(1-phenyltetrazol-5-yl)piperazin-1-yl]ethane-1,2-dione

生成物 1

HCID 24874794N1-(4-fluoro-3-(2-oxo-2-(4-(1-phenyl-1H-tetrazol-5-yl)piperazin-1-yl)acetyl)-1H-pyrrolo[2,3-c]pyridin-7-yl)-N2,N2-dimethyloxalamide収率 8.9%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

1-(7-amino-4-fluoro-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-(4-(1-phenyl-1H-tetrazol-5-yl)piperazin-1-yl)ethane-1,2-dione (100 mg, 0.23 mmol) was dissolved in DMF (2 mL) and treated with N,N-dimethyloxamic acid (27 mg, 0.23 mmol), Hunig's base (0.14 mL, 0.8 mmol) and TBTU (81 mg, 0.25 mmol). The reaction mixture was stirred at rt for 18 h. Solvent was removed in vacuum and water was added. A solid precipitated out and it was collected by filtration, dissolved in DMF and purified using reverse phase prep HPLC to afford the title compound as a pale yellow solid (11 mg). 1HNMR (500 MHz, DMSO-D6) δ 8.47 (s, 1H), 8.16 (s, 1H), 7.70-7.50 (m, 5H), 5.76 (m, 1H), 4.10-3.10 (m, 6H), 3.16 (s, 6H). LCMS: m/e 535 (M+H)+, ret time 1.33 min (method 1).

後処理

  1. customSolvent was removed in vacuum and water
  2. additionwas added
  3. customA solid precipitated out
  4. filtrationit was collected by filtration
  5. dissolutiondissolved in DMF
  6. custompurified

出典と根拠

ORDレコード
ord-4fbc90982ac14bbbba476bf1394a5a98
出典データセット
uspto-grants-2010_10
特許番号
US07807671B2

反応ノート

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