Sodium Azide → 2-(2-Aminoethyl)-6-chloro-3,4-dihydro-1,1-dioxo-7-sulfamoyl-1,2,4-benzothiadiazine

HRID 1164844

반응식

HRID 1164844 반응식
Br[CH2:2][CH2:3][N:4]1[CH2:9][NH:8][C:7]2[CH:10]=[C:11]([Cl:18])[C:12]([S:14](=[O:17])(=[O:16])[NH2:15])=[CH:13][C:6]=2[S:5]1(=[O:20])=[O:19].[N-:21]=[N+]=[N-].[Na+]>CN(C=O)C>[NH2:21][CH2:2][CH2:3][N:4]1[CH2:9][NH:8][C:7]2[CH:10]=[C:11]([Cl:18])[C:12]([S:14](=[O:17])(=[O:16])[NH2:15])=[CH:13][C:6]=2[S:5]1(=[O:20])=[O:19]

참가 물질

4

반응물 2

HCID 33557Sodium AzideHCID 142809712-(2-Bromoethyl)-6-chloro-3,4-dihydro-1,1-dioxo-7-sulfamoyl-1,2,4-benzothiadiazine

생성물 1

HCID 142809722-(2-Aminoethyl)-6-chloro-3,4-dihydro-1,1-dioxo-7-sulfamoyl-1,2,4-benzothiadiazine

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Combine the product of step A (12.2 g) with sodium azide (3.9 g) in DMF (200 ml). Stir 44 hours, extract with ethyl acetate, wash with water, dry the organic layer over MgSO4 and concentrate. Dissolve the resultant residue in ethanol (150 ml), add 5.0 g 10% Pd/C and hydrogenate at 3 atm for 4 hours. Filter and concentrate the filtrate to obtain 2-(2-aminoethyl)-6-chloro-3,4-dihydro-1,1-dioxo-7-sulfamoyl-1,2,4-benzothiadiazine. C. Treat the product of step B with N-(t-butoxycarbonyl)-(S)-aspartic acid, o-ethyl ester as described in Example 5, step A, and continue the procedure described in Example 5, steps B through F to obtain the title compound.

후처리

  1. extractionextract with ethyl acetate
  2. washwash with water
  3. dry with materialdry the organic layer over MgSO4
  4. concentrationconcentrate
  5. dissolutionDissolve the resultant residue in ethanol (150 ml)
  6. additionadd 5.0 g 10% Pd/C
  7. waithydrogenate at 3 atm for 4 hours
  8. filtrationFilter
  9. concentrationconcentrate the filtrate

출처 및 근거

ORD 기록
ord-2e8aad25ed124a5e86615de852ae4879
출처 데이터셋
uspto-grants-1990_03
특허 번호
US04906635

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