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

反応式

HRID 907525 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-1f3e0d173eb24b6a84e7c001dca0d569
出典データセット
uspto-grants-2011_09
特許番号
US08013156B2

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