Methanesulfonic Acid → 3-amino-8-bromo-1,5-dimethyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one

HRID 899402ノート

反応式

HRID 899402 の反応式
[Br:1][C:2]1[CH:26]=[CH:25][C:5]2[C:6]([CH3:24])=[N:7][CH:8]([NH:13]C(=O)OCC3C=CC=CC=3)[C:9](=[O:12])[N:10]([CH3:11])[C:4]=2[CH:3]=1.CS(O)(=O)=O.[OH-].[NH4+]>C1(OC)C=CC=CC=1>[NH2:13][CH:8]1[N:7]=[C:6]([CH3:24])[C:5]2[CH:25]=[CH:26][C:2]([Br:1])=[CH:3][C:4]=2[N:10]([CH3:11])[C:9]1=[O:12]

参加物

5

反応物 3

HCID 6395Methanesulfonic AcidHCID 14923Ammonium HydroxideHCID 21941566benzyl 8-bromo-1,5-dimethyl-2-oxo-2,3-dihydro-1H-1,4-benzodiazepin-3-ylcarbamate

生成物 1

HCID 219415543-amino-8-bromo-1,5-dimethyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one

試薬・触媒・溶媒 1

HCID 7519Anisole溶媒

反応条件

温度
40 °C

実験手順

The product of Step 3 (0.831 g, 2.00 mmol) was dissolved in anhydrous anisole (16 ml) and then methanesulfonic acid (3.84 g, 40 mmol) was added in one portion. The reaction mixture was heated to 40° C. for 30 minutes with stirring, then cooled to 0° C. in an ice bath and made basic (pH=10) with concentrated ammonium hydroxide. The aqueous solution was then extracted with chloroform (3×50 ml) and the organic layers combined, dried over magnesium sulfate, filtered and concentrated to give the crude product. Purification on silica gel, eluting with 10% methyl alcohol in chloroform, providing the title compound as an XXXX (0.463 g, 82%). 1H NMR (CDCl3, 300 MHz): δ 7.32-7.23 (m, 3 H), 4.12 (d, 1 H, J=1.1 Hz), 3.27 (s, 3 H), 2.30 (d, 3 H, J=1.5 Hz) ppm.

後処理

  1. temperaturecooled to 0° C. in an ice bath
  2. extractionThe aqueous solution was then extracted with chloroform (3×50 ml)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give the crude product
  7. customPurification on silica gel
  8. washeluting with 10% methyl alcohol in chloroform

出典と根拠

ORDレコード
ord-1b16da4397874987840b76606626bd9b
出典データセット
uspto-grants-2008_04
特許番号
US07354914B2

反応ノート

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