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

HRID 646692ノート

反応式

HRID 646692 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 21899815MeOH tetrahydrofuran溶媒

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-4f76689bc72f4beb8ea9b8b19930a429
出典データセット
uspto-grants-2010_04
特許番号
US07704995B2

反応ノート

読み込み中…