Potassium Phosphate, Tribasic → {2-[1-Methyl-5-({5-methyl-4H,5H,6H,7H-pyrazolo[1,5-a]pyrazin-2-yl}amino)-6-oxo-1,6-dihydropyridin-3-yl]-6-{6-oxo-8-thia-5 azatricyclo[7.4.0.02,7]-trideca-1(9),2(7)-dien-5-yl}phenyl}methyl Acetate

HRID 1919066ノート

反応式

HRID 1919066 の反応式
[C:1]([O:4][CH2:5][C:6]1[C:11](B2OC(C)(C)C(C)(C)O2)=[CH:10][CH:9]=[CH:8][C:7]=1[N:21]1[CH2:26][CH2:25][C:24]2[C:27]3[CH2:33][CH2:32][CH2:31][CH2:30][C:28]=3[S:29][C:23]=2[C:22]1=[O:34])(=[O:3])[CH3:2].Br[C:36]1[CH:37]=[C:38]([NH:44][C:45]2[CH:54]=[C:48]3[CH2:49][N:50]([CH3:53])[CH2:51][CH2:52][N:47]3[N:46]=2)[C:39](=[O:43])[N:40]([CH3:42])[CH:41]=1.CC(O[Na])=O.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>CC#N.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:1]([O:4][CH2:5][C:6]1[C:7]([N:21]2[C:22](=[O:34])[C:23]3[S:29][C:28]4[CH2:30][CH2:31][CH2:32][CH2:33][C:27]=4[C:24]=3[CH2:25][CH2:26]2)=[CH:8][CH:9]=[CH:10][C:11]=1[C:36]1[CH:37]=[C:38]([NH:44][C:45]2[CH:54]=[C:48]3[CH2:49][N:50]([CH3:53])[CH2:51][CH2:52][N:47]3[N:46]=2)[C:39](=[O:43])[N:40]([CH3:42])[CH:41]=1)(=[O:3])[CH3:2]

参加物

8

反応物 4

HCID 62657Potassium Phosphate, TribasicHCID 580437182-(1-oxo-3,4,5,6,7,8-hexahydrobenzothieno[2,3-c]pyridin-2(1H)-yl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl AcetateHCID 580438845-Bromo-1-methyl-3-(5-methyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-2-ylamino)pyridin-2(1H)-oneHCID 178418247HCID 178418247、化合物

生成物 1

HCID 68096607{2-[1-Methyl-5-({5-methyl-4H,5H,6H,7H-pyrazolo[1,5-a]pyrazin-2-yl}amino)-6-oxo-1,6-dihydropyridin-3-yl]-6-{6-oxo-8-thia-5 azatricyclo[7.4.0.02,7]-trideca-1(9),2(7)-dien-5-yl}phenyl}methyl Acetate収率 69%

試薬・触媒・溶媒 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 962Water溶媒HCID 6342Acetonitrile溶媒

反応条件

温度
110 °C

実験手順

A 25 mL sealed tube was charged with (2-{6-oxo-8-thia-5-azatricyclo[7.4.0.02,7]-trideca-1(9),2(7)-dien-5-yl}-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-methyl acetate 111a (571 mg, 1.2 mmol), 5-bromo-1-methyl-3-(5-methyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-2-ylamino)pyridin-2(1H)-one 146a (400 mg, 1.2 mmol), CH3COONa (195 mg, 2.4 mmol), K3PO4 (631 mg, 2.4 mmol), PdCl2(dppf) (97 mg, 0.12 mmol) suspended in CH3CN (25 mL) and H2O (1 mL). The mixture was heated at 110° C. for 2 hours. It was then evaporated and the residue was purified by column chromatography eluting with 20:1 methylene chloride/methanol to give 259a as a brown solid (500 mg, 69%). MS: (M+H)+ 613.

後処理

  1. customA 25 mL sealed tube
  2. customIt was then evaporated
  3. customthe residue was purified by column chromatography
  4. washeluting with 20:1 methylene chloride/methanol

出典と根拠

ORDレコード
ord-823123428c0b4e4789e8a3150d01938d
出典データセット
uspto-grants-2013_12
特許番号
US08618107B2

反応ノート

読み込み中…