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

HRID 899402노트

반응식

HRID 899402 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 7519Anisole용매

반응 조건

온도
40 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-1b16da4397874987840b76606626bd9b
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07354914B2

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