3,4-Dichloro-1,2,5-thiadiazole → 4-(4-Chloro-[1,2,5]thiadiazol-3-yl)-[1,4]diazepane-1-carboxylic acid tert-butyl ester

HRID 907525

반응식

HRID 907525 반응식
[N:1]1([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[Cl:15][C:16]1[C:20](Cl)=[N:19][S:18][N:17]=1>CN(C=O)C>[C:11]([O:10][C:8]([N:1]1[CH2:7][CH2:6][CH2:5][N:4]([C:20]2[C:16]([Cl:15])=[N:17][S:18][N:19]=2)[CH2:3][CH2:2]1)=[O:9])([CH3:14])([CH3:13])[CH3:12]

참가 물질

4

반응물 2

HCID 798043,4-Dichloro-1,2,5-thiadiazoleHCID 2756058Tert-butyl 1,4-diazepane-1-carboxylate

생성물 1

HCID 590139534-(4-Chloro-[1,2,5]thiadiazol-3-yl)-[1,4]diazepane-1-carboxylic acid tert-butyl ester수율 79.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
100 °C

실험 절차

A mixture of t-butyl 1-homopiperazine carboxylate (45 mmol, 9 g) and DMF (50 ml) was heated to 100° C. 3,4-dichloro-1,2,5-thiadiazole (23 mmol, 2.2 ml) was added dropwise to the mixture with stirring. The resulting mixture was stirred at 100° C. for 2 days. Mixture was quenched with ice/water and extracted with ethyl acetate (3×). The combined organic layer was washed with water (2×) and Sat. sodium chloride, dried over sodium sulfate, filtered and concentrated. The crude was purified on a silica column using 20% ethyl acetate/hexanes to give 4-(4-chloro-[1,2,5]thiadiazol-3-yl)-[1,4]diazepane-1-carboxylic acid tert-butyl ester (5.8 g). The material thus obtained was converted into the title compound by following the same procedures as in Example 1. 1H NMR (CDCl3) 9.52 (s, 2H), 7.838 (s, 2H), 7.508 (s, 1H), 7.321-7.307 (d, 2H), 6.769 (br. s, 1H), 5.464 (s, 2H), 3.925-3.851 (m, 4H), 3.820-3.790 (t, 2H), 3.612-3.582 (t, 2H), 1.987-1.959 (m, 2H) ppm.

후처리

  1. stirringThe resulting mixture was stirred at 100° C. for 2 days
  2. customMixture was quenched with ice/water
  3. extractionextracted with ethyl acetate (3×)
  4. washThe combined organic layer was washed with water (2×) and Sat. sodium chloride
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude was purified on a silica column

출처 및 근거

ORD 기록
ord-1f3e0d173eb24b6a84e7c001dca0d569
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08013156B2

연결된 노트

불러오는 중…