(S)-pentan-2-yl 2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylcarbamate → HCID 178448288、化合物

HRID 245762ノート

反応式

HRID 245762 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[C:7](B2OC(C)(C)C(C)(C)O2)[CH:6]=[CH:5][C:4]=1[NH:18][C:19](=[O:26])[O:20][C@H:21]([CH2:23][CH2:24][CH3:25])[CH3:22].COC(=O)N[CH2:31][C@H:32]1[CH2:37][CH2:36][C@H:35]([C:38]2[N:42]3[CH:43]=[CH:44][N:45]=[C:46]([CH3:47])[C:41]3=[C:40](Br)[N:39]=2)[CH2:34][CH2:33]1>>[CH3:21][O:20][C:19]([CH2:31][C@H:32]1[CH2:33][CH2:34][C@H:35]([C:38]2[N:42]3[CH:43]=[CH:44][N:45]=[C:46]([CH3:47])[C:41]3=[C:40]([C:7]3[CH:6]=[CH:5][C:4]([NH:18][C:19](=[O:26])[O:20][C@H:21]([CH2:23][CH2:24][CH3:25])[CH3:22])=[C:3]([O:2][CH3:1])[CH:8]=3)[N:39]=2)[CH2:36][CH2:37]1)=[O:26]

参加物

3

反応物 2

HCID 67364014(S)-pentan-2-yl 2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylcarbamateHCID 178502113HCID 178502113、化合物

生成物 1

HCID 178448288HCID 178448288、化合物収率 117.1%

実験手順

(S)-Pentan-2-yl 2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylcarbamate (19 mg) and methyl((trans)-4-(1-bromo-8-methylimidazo[1,5-a]pyrazin-3-yl)cyclohexyl)methylcarbamate (20 mg) were reacted according to the procedure described in example 4 step 4c and purified by prep-HPLC (column Luna C18(2); gradient acetonitrile/water with constant 0.003M trifluoroacetic acid). Proper fractions were collected and made basic with aqueous sodium hydrogencarbonate, extracted with dichloromethane, organic layer dried (Na2SO4) and concentrated in vacuo to give (S)-pentan-2-yl 4-(3-((trans)-4-(methoxycarbonylmethyl)cyclohexyl)-8-methylimidazo[1,5-a]pyrazin-1-yl)-2-methoxyphenylcarbamate (16 mg).

後処理

  1. custompurified by prep-HPLC (column Luna C18(2); gradient acetonitrile/water with constant 0.003M trifluoroacetic acid)
  2. customProper fractions were collected
  3. extractionextracted with dichloromethane, organic layer
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-54cff51c9f64422594586ebd17346b77
出典データセット
uspto-grants-2014_02
特許番号
US08658794B2

反応ノート

読み込み中…