Cesium carbonate → Tert-butyl 3,3-difluoro-5-((7-(4-morpholinophenyl)pyrido[4,3-b]pyrazin-5-ylamino)methyl)piperidine-1-carboxylate

HRID 57614

反応式

HRID 57614 の反応式
Cl[C:2]1[N:11]=[C:10]([NH:12][CH2:13][CH:14]2[CH2:19][N:18]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:17][C:16]([F:28])([F:27])[CH2:15]2)[C:9]2[C:4](=[N:5][CH:6]=[CH:7][N:8]=2)[CH:3]=1.[O:29]1[CH2:34][CH2:33][N:32]([C:35]2[CH:40]=[CH:39][C:38](B(O)O)=[CH:37][CH:36]=2)[CH2:31][CH2:30]1.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.C([O-])([O-])=O.[Cs+].[Cs+]>C(COC)OC.O.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]>[F:27][C:16]1([F:28])[CH2:15][CH:14]([CH2:13][NH:12][C:10]2[C:9]3[C:4](=[N:5][CH:6]=[CH:7][N:8]=3)[CH:3]=[C:2]([C:38]3[CH:37]=[CH:36][C:35]([N:32]4[CH2:31][CH2:30][O:29][CH2:34][CH2:33]4)=[CH:40][CH:39]=3)[N:11]=2)[CH2:19][N:18]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:17]1

参加物

7

反応物 4

HCID 10796Cesium carbonateHCID 75806TricyclohexylphosphineHCID 2795359(4-(Morpholin-4-yl)phenyl)boronic acidHCID 86717382Tert-butyl 5-((7-chloropyrido[4,3-b]pyrazin-5-ylamino)methyl)-3,3-difluoropiperidine-1-carboxylate

生成物 1

HCID 71113804Tert-butyl 3,3-difluoro-5-((7-(4-morpholinophenyl)pyrido[4,3-b]pyrazin-5-ylamino)methyl)piperidine-1-carboxylate

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 18180031Water 1,2-dimethoxyethane溶媒

反応条件

温度
160 °C

実験手順

A mixture of tert-butyl 5-((7-chloropyrido[4,3-b]pyrazin-5-ylamino)methyl)-3,3-difluoropiperidine-1-carboxylate (206 mg, 0.5 mmol), 4-morpholinophenylboronic acid (207 mg, 1.0 mmol), tri(cyclohexyl)phosphine (56 mg, 0.2 mmol), Pd2(dba)3 (91 mg, 0.1 mmol) and Cs2CO3 (325 mg, 2.0 mmol) in dimethoxyethane/H2O was sealed in a microwave reaction tube and stirred at 160° C. for 80 minutes in a microwave reactor. The mixture was cooled to room temperature, concentrated under reduced pressure, and the residue was purified by chromatography to give the title compound. MS (m/z): 541 (M+H)+.

後処理

  1. customwas sealed in a microwave reaction tube
  2. temperatureThe mixture was cooled to room temperature
  3. concentrationconcentrated under reduced pressure
  4. customthe residue was purified by chromatography

出典と根拠

ORDレコード
ord-748e2ead300e489bbc91e6741afdf325
出典データセット
uspto-grants-2016_09
特許番号
US09434726B2

関連ノート

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