ホームMCPワークベンチSkills
ホームワークベンチ通知マイページ
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
  1. ホーム
  2. /反応

Cesium carbonate → Methyl 6-(5-methoxypyrazin-2-ylamino)-4-(8-methyl-8-azabicyclo[3.2.1]octan-3-ylamino)nicotinate

HRID 384649
ノート
印刷プレビュー

反応式

HRID 384649 の反応式
Cl[C:2]1[CH:11]=[C:10]([NH:12][CH:13]2[CH2:19][CH:18]3[N:20]([CH3:21])[CH:15]([CH2:16][CH2:17]3)[CH2:14]2)[C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][N:3]=1.[CH3:22][O:23][C:24]1[N:25]=[CH:26][C:27]([NH2:30])=[N:28][CH:29]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1>>[CH3:22][O:23][C:24]1[N:25]=[CH:26][C:27]([NH:30][C:2]2[CH:11]=[C:10]([NH:12][CH:13]3[CH2:19][CH:18]4[N:20]([CH3:21])[CH:15]([CH2:16][CH2:17]4)[CH2:14]3)[C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][N:3]=2)=[N:28][CH: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

5

反応物 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 145364295-Methoxypyrazin-2-amineHCID 59613550Methyl 6-chloro-4-(8-methyl-8-azabicyclo[3.2.1]octan-3-ylamino)nicotinate

生成物 1

HCID 42610356Methyl 6-(5-methoxypyrazin-2-ylamino)-4-(8-methyl-8-azabicyclo[3.2.1]octan-3-ylamino)nicotinate
収率 15%

反応条件

温度
130 °C

実験手順

Methyl 6-chloro-4-(8-methyl-8-azabicyclo[3.2.1]octan-3-ylamino)nicotinate (26 mg, 0.084 mmol, prepared as described in Synthesis 62 and 63), 5-methoxypyrazin-2-amine (16 mg, 0.127 mmol), cesium carbonate (55 mg, 0.169 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (3.9 mg, 7 mol %), and tris(dibenzylideneacetone)dipalladium chloroform complex (3.5 mg, 3.5 mol %) were added to a vial which was flushed with nitrogen and sealed. Anhydrous toluene (0.3 mL) and DMF (0.1 mL) were added and nitrogen was bubbled through the stirred solution for 10 minutes. The mixture was heated by microwave irradiation at 130° C. for 30 minutes. The cooled solution was diluted with methanol and adsorbed onto an Isolute SCX-II column. The column was washed with methanol, then with 2M ammonia in methanol. The basic fractions concentrated. Preparative TLC, eluting with ethyl acetate-methanol-concentrated ammonia 10:1:0.2, gave methyl 6-(5-methoxypyrazin-2-ylamino)-4-(8-methyl-8-azabicyclo[3.2.1]octan-3-ylamino)nicotinate (5 mg, 15%) as an oil.

後処理

  1. customwas flushed with nitrogen
  2. customsealed
  3. additionAnhydrous toluene (0.3 mL) and DMF (0.1 mL) were added
  4. customnitrogen was bubbled through the stirred solution for 10 minutes
  5. additionThe cooled solution was diluted with methanol
  6. washThe column was washed with methanol
  7. concentrationThe basic fractions concentrated
  8. washPreparative TLC, eluting with ethyl acetate-methanol-concentrated ammonia 10:1:0.2

出典と根拠

ORDレコード
ord-0a95e6cfaf484ac2a7ce3b3fc3d69a33
出典データセット
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08367658B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート