Sodium Hydroxide → 5-[2,2-Dimethyl-6-(1-methyl-1H-pyrazol-3-ylcarbamoyl)-2,3-dihydro-benzofuran-4-yloxy]-pyridine-2-carboxylic acid

HRID 1643634노트

반응식

HRID 1643634 반응식
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][C:12]2[C:17]3[CH2:18][C:19]([CH3:22])([CH3:21])[O:20][C:16]=3[CH:15]=[C:14]([C:23](=[O:31])[NH:24][C:25]3[CH:29]=[CH:28][N:27]([CH3:30])[N:26]=3)[CH:13]=2)=[CH:7][N:6]=1)=[O:4].[OH-].[Na+]>C1COCC1>[CH3:21][C:19]1([CH3:22])[CH2:18][C:17]2[C:12]([O:11][C:8]3[CH:9]=[CH:10][C:5]([C:3]([OH:4])=[O:2])=[N:6][CH:7]=3)=[CH:13][C:14]([C:23](=[O:31])[NH:24][C:25]3[CH:29]=[CH:28][N:27]([CH3:30])[N:26]=3)=[CH:15][C:16]=2[O:20]1

참가 물질

4

반응물 2

HCID 14798Sodium HydroxideHCID 595601495-[2,2-Dimethyl-6-(1-methyl-1H-pyrazol-3-ylcarbamoyl)-2,3-dihydro-benzofuran-4-yloxy]-pyridine-2-carboxylic acid methyl ester

생성물 1

HCID 595600205-[2,2-Dimethyl-6-(1-methyl-1H-pyrazol-3-ylcarbamoyl)-2,3-dihydro-benzofuran-4-yloxy]-pyridine-2-carboxylic acid수율 79%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
60 °C

실험 절차

To a solution of 5-[2,2-dimethyl-6-(1-methyl-1H-pyrazol-3-ylcarbamoyl)-2,3-dihydro-benzofuran-4-yloxy]-pyridine-2-carboxylic acid methyl ester (179) (524 mg, 1.24 mmol) in 10 mL THF was added 2 mL 1 N aqueous NaOH. The mixture was heated at 60° C. for 1 hr, and concentrated in vacuo. The residue was acidified to pH ˜1 with 1N aqueous HCl, filtered, washed with water, and dried under vacuum at 60° C. overnight to give an off-white solid (400 mg, 79% yield). 1H NMR (400 MHz, DMSO-d6) δ 10.74 (br. s., 1 H) 8.51 (br. s., 2 H) 7.97-8.17 (m, 1 H) 7.46-7.64 (m, 2 H) 7.23 (br. s., 2 H) 6.54 (br, s, 1 H) 3.76 (s, 3 H) 2.91 (s, 2 H) 1.44 (s, 6 H); LCMS for C21H20N4O5 m/z 409.20 (M+H+).

후처리

  1. concentrationconcentrated in vacuo
  2. filtrationfiltered
  3. washwashed with water
  4. customdried under vacuum at 60° C. overnight

출처 및 근거

ORD 기록
ord-b229c5a58d9e44e6bd173052d1d679d3
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08119624B2

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