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

HRID 907521

반응식

HRID 907521 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

반응 조건

온도
100 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-b5a66ecec9fd4ade907f50778bb1964f
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08013156B2

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