Methanol → 5-[4,6-Difluoro-5-(1-methyl-1H-indol-5-yl)-1H-benzoimidazol-2-yloxy]-2-methyl-benzoic acid

HRID 1945298ノート

反応式

HRID 1945298 の反応式
C[O:2][C:3](=[O:33])[C:4]1[CH:9]=[C:8]([O:10][C:11]2[NH:15][C:14]3[CH:16]=[C:17]([F:31])[C:18]([C:21]4[CH:22]=[C:23]5[C:27](=[CH:28][CH:29]=4)[N:26]([CH3:30])[CH:25]=[CH:24]5)=[C:19]([F:20])[C:13]=3[N:12]=2)[CH:7]=[CH:6][C:5]=1[CH3:32].CO.O.[OH-].[Na+]>C1COCC1>[F:20][C:19]1[C:13]2[N:12]=[C:11]([O:10][C:8]3[CH:7]=[CH:6][C:5]([CH3:32])=[C:4]([CH:9]=3)[C:3]([OH:33])=[O:2])[NH:15][C:14]=2[CH:16]=[C:17]([F:31])[C:18]=1[C:21]1[CH:22]=[C:23]2[C:27](=[CH:28][CH:29]=1)[N:26]([CH3:30])[CH:25]=[CH:24]2

参加物

6

反応物 4

HCID 887MethanolHCID 962WaterHCID 14798Sodium Hydroxide2 回HCID 686594755-[4,6-Difluoro-5-(1-methyl-1H-indol-5-yl)-1H-benzoimidazol-2-yloxy]-2-methyl-benzoic acid methyl ester

生成物 1

HCID 452568635-[4,6-Difluoro-5-(1-methyl-1H-indol-5-yl)-1H-benzoimidazol-2-yloxy]-2-methyl-benzoic acid

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 5-[4,6-difluoro-5-(1-methyl-1H-indol-5-yl)-1H-benzoimidazol-2-yloxy]-2-methyl-benzoic acid methyl ester (655 mg, 1.464 mmol) in THF:MeOH:H2O (7 mL) was treated with sodium hydroxide (1N, 3 mL) at room temperature. After 3 h, another 3 mL of sodium hydroxide (1N) was added and stirred at room temperature for another 1.5 h, and at 50° C. for another 1.5 h. The cooled reaction solution was concentrated on a rotavapor and the resulting aqueous solution was neutralized with 1N hydrogen chloride (6 mL), and the resulting white solid was collected through filtration (washed with water) and dried under high vacuum to give the desired product as a white solid. LC-MS: calculated for C24H17F2N3O3 434.41, observed m/e 434.6 (M+H)+ (Rt 1.52 min). 1H NMR (300 MHz, DMSO-d6): δ 7.78-7.15 (m, 8H), 6.45 (d, J=3.3 Hz, 1H), 3.81 (s, 3H), 2.53 (s, 3H).

後処理

  1. waitat 50° C. for another 1.5 h
  2. customThe cooled reaction solution
  3. concentrationwas concentrated on a rotavapor
  4. filtrationthe resulting white solid was collected through filtration (washed with water)
  5. customdried under high vacuum

出典と根拠

ORDレコード
ord-1ff539ae3f3e4265b0fe5de0c7da32d9
出典データセット
uspto-grants-2013_03
特許番号
US08394969B2

反応ノート

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