Dimethyl Sulfoxide → HCID 178498839, 화합물

HRID 707364노트

반응식

HRID 707364 반응식
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

참가 물질

6

반응물 4

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 7213135Methyl 2-chloro-4-thiazolecarboxylateHCID 178479284HCID 178479284, 화합물2회

생성물 1

HCID 178498839HCID 178498839, 화합물수율 27.7%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-a5aea8449a054be9b1bca879b00ab681
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09174992B2

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