Methanol → 3-Methoxy-4-[3-(5-methyl-pyrazin-2-yl)ureido]-benzoic acid

HRID 1830720ノート

反応式

HRID 1830720 の反応式
C[O:2][C:3](=[O:23])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([NH:13][C:14]2[CH:19]=[N:18][C:17]([CH3:20])=[CH:16][N:15]=2)=[O:12])=[C:6]([O:21][CH3:22])[CH:5]=1.CO.O.[OH-].[Li+]>O>[CH3:22][O:21][C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][C:7]=1[NH:10][C:11]([NH:13][C:14]1[CH:19]=[N:18][C:17]([CH3:20])=[CH:16][N:15]=1)=[O:12])[C:3]([OH:23])=[O:2]

参加物

5

反応物 3

HCID 887MethanolHCID 168937Lithium hydroxide, monohydrateHCID 67255656HCID 67255656、化合物

生成物 1

HCID 220463633-Methoxy-4-[3-(5-methyl-pyrazin-2-yl)ureido]-benzoic acid収率 88%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
65 °C

実験手順

To a stirred suspension of 3-methoxy-4-[3-(5-methyl-pyrazin-2-yl)-ureido]-benzoic acid methyl ester (7.15 g, 22.6 mmol) in 3:1 MeOH:H2O (226 mL) at RT under N2 was added lithium hydroxide monohydrate (9.5 g, 226 mmol) as a solid and the mixture heated to 65 ° C. After reaching temperature, the suspension gradually became a bright yellow solution. After about 4 hours a precipitate formed but the reaction was continued overnight. After cooling to RT, MeOH was removed by rotovap and the aqueous suspension diluted with 100 mL H2O and neutralized to pH=5 with concentrated HCl. As pH=5 was approached, the suspension turned from yellow to white. The suspension was then filtered through paper on a large ceramic funnel. The filtration went very slowly, taking several hours. The filter cake was washed twice with H2O. When most of the H2O was removed, the residue was dried under high vacuum in a dessicator overnight to give the free acid as a white solid (6 g, 88%). 1H-NMR (400 MHz, d6-DMSO) δ 8.79 (br s, 1H), 8.36 (d, 1H), 8.22 (s, 1H), 7.57 (d, 1H), 7.51 (s, 1H), 3.97 (s, 3H), 242 (s, 3H).

後処理

  1. customAfter about 4 hours a precipitate formed
  2. temperatureAfter cooling to RT
  3. customMeOH was removed by rotovap
  4. additionthe aqueous suspension diluted with 100 mL H2O and neutralized to pH=5 with concentrated HCl
  5. filtrationThe suspension was then filtered through paper on a large ceramic funnel
  6. filtrationThe filtration
  7. waittaking several hours
  8. washThe filter cake was washed twice with H2O
  9. customWhen most of the H2O was removed
  10. customthe residue was dried under high vacuum in a dessicator overnight

出典と根拠

ORDレコード
ord-1e8dcdd5c79e492e9574d19bcfa3bb6e
出典データセット
uspto-grants-2006_06
特許番号
US07067506B2

反応ノート

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