Diisopropylethylamine → 2-[6-chloro-3-(2,2-difluoro-2-pyridin-2-yl-ethylamino)-2-oxo-2H-pyrazin-1-yl]-N-[2-(1-trityl-1H-imidazol-4-yl)-benzyl]-acetamide

HRID 1795303ノート

反応式

HRID 1795303 の反応式
[Cl:1][C:2]1[N:7]([CH2:8][C:9]([OH:11])=O)[C:6](=[O:12])[C:5]([NH:13][CH2:14][C:15]([F:23])([F:22])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)=[N:4][CH:3]=1.C(O)(=O)C(O)=O.[C:30]([N:49]1[CH:53]=[C:52]([C:54]2[CH:61]=[CH:60][CH:59]=[CH:58][C:55]=2[CH2:56][NH2:57])[N:51]=[CH:50]1)([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.Cl.CN(C)CCCN=C=NCC.ON1C2N=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C>CN(C)C=O.O>[Cl:1][C:2]1[N:7]([CH2:8][C:9]([NH:57][CH2:56][C:55]2[CH:58]=[CH:59][CH:60]=[CH:61][C:54]=2[C:52]2[N:51]=[CH:50][N:49]([C:30]([C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)([C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=3)[C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH:53]=2)=[O:11])[C:6](=[O:12])[C:5]([NH:13][CH2:14][C:15]([F:23])([F:22])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)=[N:4][CH:3]=1

参加物

8

反応物 5

HCID 81531DiisopropylethylamineHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10936874[6-Chloro-3-(2.2-difluoro-2-pyridin-2-yl-ethylamino)-2-oxo-2H-pyrazin 1-yl]-acetic AcidHCID 221851452-(1-Trityl-1h-imidazol-4-yl)-benzylamine oxalate salt

生成物 1

HCID 221851502-[6-chloro-3-(2,2-difluoro-2-pyridin-2-yl-ethylamino)-2-oxo-2H-pyrazin-1-yl]-N-[2-(1-trityl-1H-imidazol-4-yl)-benzyl]-acetamide

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

A solution of [6-chloro-3-(2,2-difluoro-2-pyridin-2-yl-ethylamino)-2-oxo-2H-pyrazin-1-yl]-acetic acid (25 mg, 0.058 mmol, preparation described in example 17), 2-(1-trityl-1H-imidazol-4-yl)-benzylamine oxalate salt (35 mg, 0.070 mmol, preparation described in example 2), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (17 mg, 0.087 mmol), 1-hydroxy-7-azabenzotriazole (12 mg, 0.087 mmol) and diisopropylethylamine (40 ul, 0.23 mmol) in N,N-dimethylformamide (1 ml) was stirred at room temperature overnight. Water was added and the reaction mixture was extracted with ethyl acetate. The combined organic layers were washed with brine. Drying and solvent evaporation gave 2-[6-chloro-3-(2,2-difluoro-2-pyridin-2-yl-ethylamino)-2-oxo-2H-pyrazin-1-yl]-N-[2-(1-trityl-1H-imidazol-4-yl)-benzyl]-acetamide; 1H NMR (CDCl3, 300 MHz) δ 9.11 (m, 1H), 8.65 (d, 1H, J=4.6 Hz), 8.02 (s, 1H), 7.80 (m, 1H), 7.61 (m, 1H), 7.47 (m, 1H), 7.38–7.15 (m, 18H), 6.99 (d, 1H, J=1.2 Hz), 6.78 (s, 1H), 6.36 (m, 1H), 4.78 (s, 2H), 4.43 (d, 2H, J=6.4 Hz), 4.14 (m, 2H).

後処理

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. customDrying
  4. customsolvent evaporation

出典と根拠

ORDレコード
ord-5a37467e75204b2190ca767a59b36088
出典データセット
uspto-grants-2006_04
特許番号
US07026324B2

反応ノート

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