Diisopropylethylamine → HCID 178429379, 화합물

HRID 707383

반응식

HRID 707383 반응식
Cl.Cl.[NH2:3][C@H:4]1[CH2:7][C@H:6]([N:8]2[C:12]3=[N:13][CH:14]=[CH:15][N:16]=[C:11]3[C:10]([CH3:18])([CH3:17])[C:9]2=[O:19])[CH2:5]1.C(N(C(C)C)C(C)C)C.CS([C:33]1[S:34][C:35]2[C:40]([N:41]=1)=[CH:39][CH:38]=[CH:37][N:36]=2)(=O)=O>CS(C)=O.CCOC(C)=O.O>[CH3:18][C:10]1([CH3:17])[C:11]2[C:12](=[N:13][CH:14]=[CH:15][N:16]=2)[N:8]([C@H:6]2[CH2:7][C@H:4]([NH:3][C:33]3[S:34][C:35]4[C:40]([N:41]=3)=[CH:39][CH:38]=[CH:37][N:36]=4)[CH2:5]2)[C:9]1=[O:19]

참가 물질

7

반응물 3

HCID 81531DiisopropylethylamineHCID 36045032-(Methylsulfonyl)thiazolo[5,4-b]pyridine2회HCID 178429369HCID 178429369, 화합물2회

생성물 1

HCID 178429379HCID 178429379, 화합물수율 60.5%

시약·촉매·용매 3

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매HCID 8857Ethyl Acetate용매

반응 조건

온도
100 °C

실험 절차

A mixture of 5-(trans-3-aminocyclobutyl)-7,7-dimethyl-5H-pyrrolo[2,3-b]pyrazin-6(7H)-one dihydrochloride (Intermediate 83, 51 mg, 0.167 mmol), N-ethyl-N-isopropylpropan-2-amine (102 μl, 0.585 mmol), and 2-(methylsulfonyl)thiazolo[5,4-b]pyridine (Intermediate 76) (43.0 mg, 0.201 mmol) in DMSO (0.3 ml) was stirred at 100° C. for 3 h. The mixture was diluted with EtOAc and water in a separatory funnel. The aqueous layer was extracted with EtOAc twice. The combined organic layer was dried over Na2SO4 and concentrated in vacuo. The crude solution was purified by silica gel chromatography (ISCO 12 g, 0-70% EtOAc-hexane) to give 7,7-dimethyl-5-(trans-3-(thiazolo[5,4-b]pyridin-2-ylamino)cyclobutyl)-5H-pyrrolo[2,3-b]pyrazin-6(7H)-one (37 mg, 0.101 mmol, 60.4% yield) as off-white solid. 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 1.46 (s, 6 H) 2.50 (ddd, J=14.03, 9.35, 3.51 Hz, 2 H) 3.37-3.55 (m, 2 H) 5.30 (t, J=8.48 Hz, 1 H) 5.73 (br. s., 1 H) 7.17-7.25 (m, 1 H) 7.74 (dd, J=8.04, 1.46 Hz, 1 H) 8.05-8.16 (m, 2 H) 8.22 (dd, J=4.75, 1.53 Hz, 1 H).

후처리

  1. extractionThe aqueous layer was extracted with EtOAc twice
  2. dry with materialThe combined organic layer was dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe crude solution was purified by silica gel chromatography (ISCO 12 g, 0-70% EtOAc-hexane)

출처 및 근거

ORD 기록
ord-cba2053e67e34362bcc5567ab35ee0e6
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09174992B2

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