Sodium Hydroxide → Quinoxaline-6-carboxylic acid

HRID 717039

반응식

HRID 717039 반응식
O1C2C=CC([C:10]3[C:19](N4CCC[C@@H]4C)=[N:18][C:17]4[C:12](=[CH:13][CH:14]=[C:15]([C:26]([O:28]C)=[O:27])[CH:16]=4)[N:11]=3)=CC=2OC1.[OH-].[Na+]>CO.O>[N:11]1[C:12]2[C:17](=[CH:16][C:15]([C:26]([OH:28])=[O:27])=[CH:14][CH:13]=2)[N:18]=[CH:19][CH:10]=1

참가 물질

5

반응물 2

HCID 14798Sodium HydroxideHCID 67042044methyl 2-(benzo[d][1,3]dioxol-5-yl)-3-((S)-2-methylpyrrolidin-1-yl)quinoxaline-6-carboxylate

생성물 1

HCID 674813Quinoxaline-6-carboxylic acid

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

실험 절차

Into a 50-mL round-bottom flask, was placed a solution of methyl 2-(benzo[d][1,3]dioxol-5-yl)-3-((S)-2-methylpyrrolidin-1-yl)quinoxaline-6-carboxylate (94 mg, 0.24 mmol, 1.00 equiv) in methanol (15 mL). This was followed by the addition of a solution of sodium hydroxide (58.9 mg, 1.47 mmol, 5.00 equiv) in water (3 mL) dropwise with stirring. The resulting solution was stirred for 5 hr at 50° C. in an oil bath. The resulting mixture was concentrated under vacuum. The resulting solution was diluted with H2O. The pH value of the aqueous solution was adjusted to 3-4 with 1N aqueous hydrogen chloride. The resulting solids were collected by filtration. The crude product (100 mg) was purified by Prep-HPLC with the following conditions (1#-Waters 2767-2): Column, SunFire Prep C18, 19*150 mm 5 um; mobile phase, water with 0.05% TFA and CH3CN (10% CH3CN up to 80% in 8.5 min, hold 80% in 1 min, up to 100% in 0.1 min, hold 100% in 0.8 min); Detector, UV 220&254 nm. This resulted in 40 mg (44%) of 2-(benzo[d][1,3]dioxol-5-yl)-3-(S)-2-methylpyrrolidin-1-yl)quinoxaline-6-carboxylic acid as a yellow solid.

후처리

  1. customInto a 50-mL round-bottom flask, was placed
  2. stirringThe resulting solution was stirred for 5 hr at 50° C. in an oil bath
  3. concentrationThe resulting mixture was concentrated under vacuum
  4. additionThe resulting solution was diluted with H2O
  5. filtrationThe resulting solids were collected by filtration
  6. customThe crude product (100 mg) was purified by Prep-HPLC with the following conditions (1#-Waters 2767-2)
  7. customin 1 min
  8. waitup to 100% in 0.1 min
  9. customin 0.8 min

출처 및 근거

ORD 기록
ord-658706be6cad443da11f6075cb6774ba
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09193693B2

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