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1-Methyl-4-(pyrrolidin-2-yl)piperidine → 2-(1-isopropyl-3-methyl-1H-1,2,4-triazol-5-yl)-9-(2-(1-methylpiperidin-4-yl)pyrrolidin-1-yl)-5,6-dihydroimidazo[1,2-d]pyrido[3,4-f][1,4]oxazepine

HRID 1530639
ノート
印刷プレビュー

反応式

HRID 1530639 の反応式
Cl[C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][N:15]=1)[C:12]1[N:8]([CH:9]=[C:10]([C:16]3[N:20]([CH:21]([CH3:23])[CH3:22])[N:19]=[C:18]([CH3:24])[N:17]=3)[N:11]=1)[CH2:7][CH2:6][O:5]2.[CH3:25][N:26]1[CH2:31][CH2:30][CH:29]([CH:32]2[CH2:36][CH2:35][CH2:34][NH:33]2)[CH2:28][CH2:27]1.CC([O-])(C)C.[Na+]>CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C.C1(C)C=CC=CC=1>[CH:21]([N:20]1[C:16]([C:10]2[N:11]=[C:12]3[C:13]4[CH:14]=[N:15][C:2]([N:33]5[CH2:34][CH2:35][CH2:36][CH:32]5[CH:29]5[CH2:28][CH2:27][N:26]([CH3:25])[CH2:31][CH2:30]5)=[CH:3][C:4]=4[O:5][CH2:6][CH2:7][N:8]3[CH:9]=2)=[N:17][C:18]([CH3:24])=[N:19]1)([CH3:23])[CH3:22]
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

6

反応物 3

HCID 45663131-Methyl-4-(pyrrolidin-2-yl)piperidineHCID 23676156Sodium t-butoxideHCID 8893255312-chloro-4-[3-methyl-1-(propan-2-yl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6,13-triazatricyclo[8.4.0.02,6]tetra-deca1(14),2,4,10,12-pentaene

生成物 1

HCID 665589212-(1-isopropyl-3-methyl-1H-1,2,4-triazol-5-yl)-9-(2-(1-methylpiperidin-4-yl)pyrrolidin-1-yl)-5,6-dihydroimidazo[1,2-d]pyrido[3,4-f][1,4]oxazepine

試薬・触媒・溶媒 2

HCID 178418851
HCID 178418851、化合物
触媒
HCID 1140Toluene溶媒

反応条件

温度
110 °C

実験手順

A 10 mL microwave vial was charged with 12-chloro-4-[3-methyl-1-(propan-2-yl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6,13-triazatricyclo[8.4.0.02,6]tetradeca1(14), 2,4,10,12-Pentaene (160 mg, 0.470 mmol), toluene (4 mL), 1-methyl-4-(pyrrolidin-2-yl)piperidine (156 mg, 0.94 mmol), Pd(PtBu3)2(27 mg, 0.047 mmol), NaOtBu (135 mg, 1.40 mmol). The vial was sealed and degassed with N2 for three times. The resulting mixture was stirred at 110° C. for 1 h. After concentration, the residue was purified by reverse phase Combiflash eluting with a 0-50% gradient of CH3CN in 0.3% NH4HCO3 to give 249, which was separated by chiral HPLC (AD column, 30% EtOH (0.1% DEA) in n-hexane isocratic) to give: 9 mg of one enantiomer and 6 mg of the other (7% total yield)

後処理

  1. customThe vial was sealed
  2. customdegassed with N2 for three times
  3. concentrationAfter concentration
  4. customthe residue was purified by reverse phase Combiflash
  5. washeluting with a 0-50% gradient of CH3CN in 0.3% NH4HCO3

出典と根拠

ORDレコード
ord-daa791be0aca42428d0ebe5f344413f4
出典データセット
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09090628B2

反応ノート

読み込み中…

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