Dimethyl Sulfoxide → HCID 178498839、化合物

HRID 707364ノート

反応式

HRID 707364 の反応式
Cl.[NH2:2][C@H:3]1[CH2:6][C@H:5]([N:7]2[C:11]3=[N:12][CH:13]=[CH:14][N:15]=[C:10]3[N:9]([CH:16]3[CH2:18][CH2:17]3)[C:8]2=[O:19])[CH2:4]1.ClC1SC=C([C:26]([O:28][CH3:29])=[O:27])N=1.C([N:33]([CH:36]([CH3:38])C)[CH2:34]C)(C)C.C[S:40](C)=O>O>[CH:16]1([N:9]2[C:10]3[C:11](=[N:12][CH:13]=[CH:14][N:15]=3)[N:7]([C@H:5]3[CH2:6][C@H:3]([NH:2][C:34]4[S:40][C:38]([C:26]([O:28][CH3:29])=[O:27])=[CH:36][N:33]=4)[CH2:4]3)[C:8]2=[O:19])[CH2:17][CH2:18]1

参加物

6

反応物 4

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 7213135Methyl 2-chloro-4-thiazolecarboxylateHCID 178479284HCID 178479284、化合物2 回

生成物 1

HCID 178498839HCID 178498839、化合物収率 27.7%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A solution of 1-(trans-3-aminocyclobutyl)-3-cyclopropyl-1H-imidazo[4,5-b]pyrazin-2(3H)-one hydrochloride (Intermediate 79, 1.00 g, 3.55 mmol), methyl 2-chloro-4-thiazolecarboxylate (0.820 g, 4.61 mmol), and diisopropylethylamine (3.09 mL, 17.75 mmol) in DMSO (10 mL) was stirred at 120° C. for 18 h. The reaction was allowed to cool to room temperature, diluted with water and extracted with EtOAc. EtOAc was concentrated and residue purified with ISCO using silica gel column eluting with 0-70% EtOAc/hexane to give the title compound methyl 2-((trans-3-(3-cyclopropyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyrazin-1-yl)cyclobutyl)amino)thiazole-5-carboxylate (0.380 g, 0.983 mmol, 27.7% yield). m/z: 387.0 (M+1); 1H NMR (400 MHz, DMSO-d6) δ: ppm 8.38 (d, J=6.46 Hz, 1 H), 7.99 (q, J=3.26 Hz, 2 H), 7.60 (s, 1 H), 5.15 (t, J=8.31 Hz, 1 H), 4.28-4.47 (m, 1 H), 3.77 (s, 3 H), 3.18-3.30 (m, 2 H), 2.88-3.07 (m, 1 H), 2.34-2.47 (m, 2 H), 0.91-1.13 (m, 4 H).

後処理

  1. extractionextracted with EtOAc
  2. concentrationEtOAc was concentrated
  3. customresidue purified with ISCO
  4. washeluting with 0-70% EtOAc/hexane

出典と根拠

ORDレコード
ord-a5aea8449a054be9b1bca879b00ab681
出典データセット
uspto-grants-2015_11
特許番号
US09174992B2

反応ノート

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