Pyridine → N-(6-(7-azabicyclo[2.2.1]heptan-7-yl)-4-methylpyridin-3-yl)-5-methyl-4-oxo-1,4-dihydroquinoline-3-carboxamide

HRID 1911875ノート

反応式

HRID 1911875 の反応式
[CH3:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4](=[O:15])[C:5]([C:12]([OH:14])=O)=[CH:6][NH:7]2.[CH:16]12[N:22]([C:23]3[N:28]=[CH:27][C:26]([NH2:29])=[C:25]([CH3:30])[CH:24]=3)[CH:19]([CH2:20][CH2:21]1)[CH2:18][CH2:17]2.N1C=CC=CC=1>CC1CCCO1.C(OCC)(=O)C>[CH:16]12[N:22]([C:23]3[N:28]=[CH:27][C:26]([NH:29][C:12]([C:5]4[C:4](=[O:15])[C:3]5[C:8](=[CH:9][CH:10]=[CH:11][C:2]=5[CH3:1])[NH:7][CH:6]=4)=[O:14])=[C:25]([CH3:30])[CH:24]=3)[CH:19]([CH2:20][CH2:21]1)[CH2:18][CH2:17]2

参加物

6

反応物 3

HCID 1049PyridineHCID 156185565-Methyl-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 593162336-(7-Azabicyclo[2.2.1]heptan-7-yl)-4-methylpyridin-3-amine

生成物 1

HCID 45259022N-(6-(7-azabicyclo[2.2.1]heptan-7-yl)-4-methylpyridin-3-yl)-5-methyl-4-oxo-1,4-dihydroquinoline-3-carboxamide収率 26.2%

試薬・触媒・溶媒 2

HCID 73012-Methyltetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 5-methyl-4-oxo-1H-quinoline-3-carboxylic acid (60 mg, 0.2953 mmol) and 6-(7-azabicyclo[2.2.1]heptan-7-yl)-4-methyl-pyridin-3-amine (60.03 mg, 0.2953 mmol) in 2-methyltetrahydrofuran (1 mL) was added propyl phosphonic acid cyclic anhydride (375.8 μL of 50% w/v, 0.5906 mmol) followed by pyridine (46.72 mg, 47.77 μL, 0.5906 mmol). The mixture was irradiated under microwave conditions for 1 h at 100° C. The crude reaction mixture was diluted with ethyl acetate (2 mL) and quenched with 10% NaHCO3 solution (3 mL). The resulting precipitate was filtered and washed with ethyl acetate (5 mL). The solid was resuspended in 20% aqueous Na2CO3 (5 mL)/methanol (2 mL) and stirred for 30 min. The solid was filtered, rinsed with water and air dried to provide N-(6-(7-azabicyclo[2.2.1]heptan-7-yl)-4-methylpyridin-3-yl)-5-methyl-4-oxo-1,4-dihydroquinoline-3-carboxamide (30 mg, 26% yield). LC/MS m/z 389.4 [M+H]+, retention time 1.33 min (RP-C18, 10-99% CH3CN/0.05% TFA over 3 min).

後処理

  1. customThe mixture was irradiated under microwave conditions for 1 h at 100° C
  2. customThe crude reaction mixture
  3. customquenched with 10% NaHCO3 solution (3 mL)
  4. filtrationThe resulting precipitate was filtered
  5. washwashed with ethyl acetate (5 mL)
  6. filtrationThe solid was filtered
  7. washrinsed with water and air
  8. customdried

出典と根拠

ORDレコード
ord-8d8375a445114f85819093cb7d8c6ced
出典データセット
uspto-grants-2013_12
特許番号
US08604203B2

反応ノート

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