Lithium Hydroxide → 3-(4-(6-(5,7-Dimethoxy-4-oxo-3,4-dihydroquinazolin-2-yl)pyridin-2-yl)piperazin-1-yl)propanoic acid

HRID 1519423ノート

反応式

HRID 1519423 の反応式
[CH3:1][O:2][C:3]1[CH:12]=[C:11]([O:13][CH3:14])[CH:10]=[C:9]2[C:4]=1[C:5](=[O:33])[NH:6][C:7]([C:15]1[N:20]=[C:19]([N:21]3[CH2:26][CH2:25][N:24]([CH2:27][CH2:28][C:29]([O:31]C)=[O:30])[CH2:23][CH2:22]3)[CH:18]=[CH:17][CH:16]=1)=[N:8]2.[OH-].[Li+]>C1COCC1.O.CO>[CH3:1][O:2][C:3]1[CH:12]=[C:11]([O:13][CH3:14])[CH:10]=[C:9]2[C:4]=1[C:5](=[O:33])[NH:6][C:7]([C:15]1[N:20]=[C:19]([N:21]3[CH2:22][CH2:23][N:24]([CH2:27][CH2:28][C:29]([OH:31])=[O:30])[CH2:25][CH2:26]3)[CH:18]=[CH:17][CH:16]=1)=[N:8]2

参加物

6

反応物 2

HCID 3939Lithium HydroxideHCID 136408150Methyl 3-(4-(6-(5,7-dimethoxy-4-oxo-3,4-dihydroquinazolin-2-yl)pyridin-2-yl)piperazin-1-yl)propanoate

生成物 1

HCID 1362488433-(4-(6-(5,7-Dimethoxy-4-oxo-3,4-dihydroquinazolin-2-yl)pyridin-2-yl)piperazin-1-yl)propanoic acid収率 83%

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of methyl 3-(4-(6-(5,7-dimethoxy-4-oxo-3,4-dihydroquinazolin-2-yl)pyridin-2-yl)piperazin-1-yl)propanoate (0.200 g, 0.44 mmol) in THF (10 mL), water (5 mL) and methanol (3 mL) was added lithium hydroxide (0.053 g, 2.21 mmol). The reaction was stirred for 2 h at rt. After that time the reaction was concentrated under reduced pressure, diluted with water (5 mL) and acidified using 1N HCl to pH 4.5-5.0. The precipitated solids were collected by filtration, washed with water and dried under high vacuum to give 3-(4-(6-(5,7-dimethoxy-4-oxo-3,4-dihydroquinazolin-2-yl)pyridin-2-yl)piperazin-1-yl)propanoic acid (0.160 g, 83%) as a yellow solid: mp 241° C. dec.; 1H NMR (400 MHz, DMSO-d6) δ 11.15 (s, 1H), 7.68-7.80 (m, 2H), 7.09 (d, J=8.20 Hz, 1H), 6.78 (d, J=1.95 Hz, 1H), 6.58 (d, J=1.95 Hz, 1H), 3.91 (s, 3H), 3.86 (s, 3H), 3.73 (br s, 4H), 2.77-2.85 (m, 2H), 2.73 (br s, 4H), 2.55 (t, J=7.22 Hz, 2H); ESI MS m/z 440 [M+H]+.

後処理

  1. concentrationAfter that time the reaction was concentrated under reduced pressure
  2. additiondiluted with water (5 mL)
  3. filtrationThe precipitated solids were collected by filtration
  4. washwashed with water
  5. customdried under high vacuum

出典と根拠

ORDレコード
ord-fffbcaa3bd0f489595c9485debcf7bc2
出典データセット
uspto-grants-2015_07
特許番号
US09073878B2

反応ノート

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