Diisopropylethylamine → HCID 178429379、化合物

HRID 707383ノート

反応式

HRID 707383 の反応式
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]

参加物

7

反応物 3

HCID 81531DiisopropylethylamineHCID 36045032-(Methylsulfonyl)thiazolo[5,4-b]pyridine2 回HCID 178429369HCID 178429369、化合物2 回

生成物 1

HCID 178429379HCID 178429379、化合物収率 60.5%

試薬・触媒・溶媒 3

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-cba2053e67e34362bcc5567ab35ee0e6
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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