Hydrochloric Acid → 5-{5-Amino-6-[(methylamino)carbonyl]pyrazin-2-yl}-2-chlorobenzoic acid

HRID 646692노트

반응식

HRID 646692 반응식
[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:12]2[CH:13]=[CH:14][C:15]([Cl:22])=[C:16]([CH:21]=2)[C:17]([O:19]C)=[O:18])=[N:6][C:7]=1[C:8]([NH:10][CH3:11])=[O:9].[OH-].[Na+].Cl>CO.O1CCCC1.C(OCC)(=O)C>[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:12]2[CH:13]=[CH:14][C:15]([Cl:22])=[C:16]([CH:21]=2)[C:17]([OH:19])=[O:18])=[N:6][C:7]=1[C:8]([NH:10][CH3:11])=[O:9]

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 68651344Methyl 5-{5-amino-6-[(methylamino)carbonyl]pyrazin-2-yl}-2-chlorobenzoate

생성물 1

HCID 686515865-{5-Amino-6-[(methylamino)carbonyl]pyrazin-2-yl}-2-chlorobenzoic acid수율 48%

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 21899815MeOH tetrahydrofuran용매

실험 절차

To a solution of methyl 5-{5-amino-6-[(methylamino)carbonyl]pyrazin-2-yl}-2-chlorobenzoate (96 mg, 31 mmol) in methanol/tetrahydrofuran (1:1, 5.0 mL) was added 2.0 N aqueous sodium hydroxide (0.16 g, 4.00 mmol). The reaction was stirred overnight at room temperature. Reaction was neutralized with 2.0 N aqueous hydrochloric acid (4 mL) and diluted with ethyl acetate (100 mL). The organic layer was washed with water (20 mL), saturated aqueous sodium chloride (30 mL), dried over magnesium sulfate, filtered, and concentrated to afford 5-{5-amino-6-[(methylamino)carbonyl]pyrazin-2-yl}-2-chlorobenzoic acid (45 mg, 48% yield). 1H NMR (400 MHz, d6-DMSO): 13.42 (br s, 1H), 8.90 (br s, 1H), 8.45 (d, 1H), 8.32 (dd, 1H), 7.85 (br s, 2H), 7.60 (d, 2H), 2.82 (s, 3H); MS (EI) for C13H11N4O3Cl: 307 (MH+).

후처리

  1. customReaction
  2. washThe organic layer was washed with water (20 mL), saturated aqueous sodium chloride (30 mL)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-4f76689bc72f4beb8ea9b8b19930a429
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07704995B2

반응 노트

불러오는 중…