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llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.8.0
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Potassium Phosphate, Tribasic → 7-(2-Aminopyrimidin-5-yl)-1-{[(1r)-1-cyclopropyl-2,2,2-trifluoroethyl]amino}-5h-pyrido[4,3-b]indole-4-carboxamide

HRID 1970996
ノート
印刷プレビュー

反応式

HRID 1970996 の反応式
Cl[C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[C:14]([NH:15][C@H:16]([CH:21]4[CH2:23][CH2:22]4)[C:17]([F:20])([F:19])[F:18])=[N:13][CH:12]=[C:11]([C:24]([NH2:26])=[O:25])[C:7]=3[NH:8][C:9]=2[CH:10]=1.[NH2:27][C:28]1[N:33]=[CH:32][C:31](B2OC(C)(C)C(C)(C)O2)=[CH:30][N:29]=1.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1CCOCC1>[NH2:27][C:28]1[N:33]=[CH:32][C:31]([C:2]2[CH:3]=[CH:4][C:5]3[C:6]4[C:14]([NH:15][C@H:16]([CH:21]5[CH2:22][CH2:23]5)[C:17]([F:19])([F:18])[F:20])=[N:13][CH:12]=[C:11]([C:24]([NH2:26])=[O:25])[C:7]=4[NH:8][C:9]=3[CH:10]=2)=[CH:30][N:29]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 177502122-Aminopyrimidine-5-boronic acid, pinacol esterHCID 565954477-Chloro-1-{[(1R)-1-cyclopropyl-2,2,2-trifluoroethyl]amino}-5H-pyrido[4,3-b]indole-4-carboxamide

生成物 1

HCID 426229347-(2-Aminopyrimidin-5-yl)-1-{[(1r)-1-cyclopropyl-2,2,2-trifluoroethyl]amino}-5h-pyrido[4,3-b]indole-4-carboxamide

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

7-Chloro-1-{[(1R)-1-cyclopropyl-2,2,2-trifluoroethyl]amino}-5H-pyrido[4,3-b]indole-4-carboxamide (8.36 g, 21.8 mmol) and 2-aminopyrimidine-5-boronic acid pinacol ester (7.73 g, 34.9 mmol) were placed in a flask. Pd2(dba)3 (2.0 g, 2.184 mmol), tricyclohexylphosphine (1.53 g, 5.46 mmol), dioxane (437 ml) and K3PO4 (1.25 M in water, 59.2 ml, 74.0 mmol) were added and the flask purged with N2 for 15 min. The reaction mixture was heated at 100° C. for 4 h, and cooled to room temperature. The mixture was diluted with EtOAc, washed with water and brine, dried (magnesium sulfate), and concentrated. Flash chromatography gave the title compound as a white solid. 1H NMR (600 MHz, CD3SOCD3) δ 11.64 (s, 1H); 8.62 (s, 2H); 8.54 (d, 1H); 8.52 (s, 1H); 7.97 (br s, 1H); 7.95 (d, 1H); 7.53 (dd, 1H); 7.30 (br s, 1H); 7.01 (d, 1H); 6.79 (s, 2H); 4.87 (m, 1H); 1.62 (m, 1H); 0.76 (m, 1H); 0.64 (m, 1H); 0.55 (m, 1H); 0.35 (m, 1H). LRMS (APCI) calc'd for (C21H18F3N7O) [M+H]+, 442.2. found 442.1.

後処理

  1. customthe flask purged with N2 for 15 min
  2. temperaturecooled to room temperature
  3. additionThe mixture was diluted with EtOAc
  4. washwashed with water and brine
  5. dry with materialdried (magnesium sulfate)
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-bbd2a2d8d04a46c6a2d313663d321120
出典データセット
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08431569B2

反応ノート

読み込み中…

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