Lithium Hydroxide → HCID 59618129、化合物

HRID 449938ノート

反応式

HRID 449938 の反応式
[Cl:1][C:2]1[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[C:3]=1[C:4]([NH:6][C:7]1[N:12]=[CH:11][N:10]=[C:9]([NH:13][C:14]2[CH:24]=[CH:23][C:17]([C:18]([O:20]CC)=[O:19])=[CH:16][CH:15]=2)[CH:8]=1)=[O:5].[Li+].[OH-]>C1COCC1>[Cl:1][C:2]1[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[C:3]=1[C:4]([NH:6][C:7]1[N:12]=[CH:11][N:10]=[C:9]([NH:13][C:14]2[CH:24]=[CH:23][C:17]([C:18]([OH:20])=[O:19])=[CH:16][CH:15]=2)[CH:8]=1)=[O:5]

参加物

4

反応物 2

HCID 3939Lithium HydroxideHCID 59618316HCID 59618316、化合物

生成物 1

HCID 59618129HCID 59618129、化合物収率 92%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
60 °C

実験手順

To a solution of ethyl 4-(6-(2,6-dichlorobenzamido)pyrimidin-4-ylamino)benzoate (0.279 g, 0.647 mmol) in THF (5 mL) was added a solution of 3 N LiOH (2 mL). The mixture was heated at 60° C. for 12 hrs. THF was removed under reduced pressure. The residue was diluted with water, acidified with 1 N HCl to pH 3.0. The precipitated white solid was collected by filtration, washed with water, dried in high vacuum to give 4-(6-(2,6-dichlorobenzamido)pyrimidin-4-ylamino)benzoic acid (0.24 g, yield: 92%). 1H NMR (500 MHz, DMSO) δ 12.52 (s, 1H), 11.41 (s, 1H), 10.07 (s, 1H), 8.53 (s, 1H), 7.90 (d, J=8.9 Hz, 2H), 7.85 (d, J=8.9 Hz, 2H), 7.78 (d, J=0.8 Hz, 1H), 7.58-7.53 (m, 2H), 7.49 (dd, J=9.1, 6.9 Hz, 1H). LCMS (ESI) m/z: 403.0 [M+H+].

後処理

  1. customTHF was removed under reduced pressure
  2. additionThe residue was diluted with water
  3. filtrationThe precipitated white solid was collected by filtration
  4. washwashed with water
  5. customdried in high vacuum

出典と根拠

ORDレコード
ord-48a7fed144eb4deab421dc6780dd20ce
出典データセット
uspto-grants-2013_07
特許番号
US08486950B2

反応ノート

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