Hydrochloric Acid → Tert-butyl 4-(4-chloro-1,2,5-thiadiazol-3-yl)piperazine-1-carboxylate

HRID 907521

反応式

HRID 907521 の反応式
[C:1]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[Cl:14][C:15]1[C:19](Cl)=[N:18][S:17][N:16]=1.Cl>CN(C=O)C.O>[C:4]([O:3][C:1]([N:8]1[CH2:9][CH2:10][N:11]([C:19]2[C:15]([Cl:14])=[N:16][S:17][N:18]=2)[CH2:12][CH2:13]1)=[O:2])([CH3:7])([CH3:6])[CH3:5]

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 798043,4-Dichloro-1,2,5-thiadiazoleHCID 143452tert-Butyl piperazine-1-carboxylate

生成物 1

HCID 15524001Tert-butyl 4-(4-chloro-1,2,5-thiadiazol-3-yl)piperazine-1-carboxylate収率 83%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

1-Boc-piperazine (30.2 g, 165 mmol) was dissolved in DMF (30.0 mL) and heated to 100° C. 3,4-Dichloro-1,2,5-thiadiazole (7.5 mL, 80 mmol) was added dropwise with stirring and the mixture heated at 100° C. for 5.5 h. The reaction mixture was diluted with H2O and the pH adjusted to 2.0 with 1N HCl. The resulting solids were filtered, washed with H2O and dried under vacuum to give 20.1 g (83%) of 4-(4-chloro-[1,2,5]thiadiazol-3-yl)-piperazine-1-carboxylic acid tert-butyl ester as a tan solid. 1H NMR (DMSO-d6) 3.48 (m, 4H), 3.36 (m, 4H), 1.42 (s, 9H) ppm. LC-MS (MH+)=205 (-Boc).

後処理

  1. temperaturethe mixture heated at 100° C. for 5.5 h
  2. filtrationThe resulting solids were filtered
  3. washwashed with H2O
  4. customdried under vacuum

出典と根拠

ORDレコード
ord-b5a66ecec9fd4ade907f50778bb1964f
出典データセット
uspto-grants-2011_09
特許番号
US08013156B2

関連ノート

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