Ammonia → Ether 3-[4-(3-amino-5-bromopyrid-2-yl)butylamino]-4-amino-1,2,5-thiadiazole-1-oxide

HRID 1607064

반응식

HRID 1607064 반응식
CO[C:3]1[C:7]([O:8][CH3:9])=NS(=O)[N:4]=1.N[C:12]1C(CCCCN)=NC=C(Br)C=1.[NH2:24][C:25]1[C:26]([CH2:32][CH2:33][CH2:34][CH2:35][NH:36][C:37]2[C:41](OC)=[N:40][S:39](=[O:44])[N:38]=2)=[N:27][CH:28]=[C:29]([Br:31])[CH:30]=1.NC1C(C2(OC)NS(=O)N=C2)=NC=C(Br)C=1.N>CO.C(Cl)(Cl)Cl>[CH3:3][CH2:7][O:8][CH2:9][CH3:12].[NH2:24][C:25]1[C:26]([CH2:32][CH2:33][CH2:34][CH2:35][NH:36][C:37]2[C:41]([NH2:4])=[N:40][S:39](=[O:44])[N:38]=2)=[N:27][CH:28]=[C:29]([Br:31])[CH:30]=1

참가 물질

8

반응물 5

HCID 222AmmoniaHCID 129139473,4-Dimethoxy-1,2,5-thiadiazole 1-oxideHCID 145374593-Amino-5-bromo-(4-aminobutyl)pyridineHCID 159623603-[4-(3-Amino-5-bromopyrid-2-yl)butylamino]-4-methoxy-1,2,5-thiadiazole-1-oxideHCID 867433534-(3-Amino-5-bromopyrid-2-yl)-4-methoxy-1,2,5-thiadiazole-1-oxide

생성물 1

HCID 86740210Ether 3-[4-(3-amino-5-bromopyrid-2-yl)butylamino]-4-amino-1,2,5-thiadiazole-1-oxide수율 9.7%

시약·촉매·용매 2

HCID 887Methanol용매2회HCID 6212Chloroform용매

실험 절차

A solution of 3,4-dimethoxy-1,2,5-thiadiazole-1-oxide (0.995 g) in methanol (25 ml) was reacted with a solution of 3-amino-5-bromo-(4-aminobutyl)pyridine (1.5 g) in methanol (25 ml) at room temperature for 3 hours. The solvent was removed in vacuo and the residue was chromatographed on silica in ethanol to give an oil which was triturated with ether and recrystallised from ethanol/ether to give 3-[4-(3-amino-5-bromopyrid-2-yl) butylamino]-4-methoxy-1,2,5-thiadiazole-1-oxide (1.7 g) m.p. 118°-120° C. (g) Reaction of 3-[4-(3-amino-5-bromopyrid-2-yl)-4-methoxy-1,2,5-thiadiazole-1-oxide (0.56 g) with methanolic ammonia solution (50 ml) at room temperature overnight gave after chromatography on silica in chloroform and trituration with ether 3-[4-(3-amino-5-bromopyrid-2-yl)butylamino]-4-amino-1,2,5-thiadiazole-1-oxide (0.19 g) m.p. 105°-109° C.

후처리

  1. customThe solvent was removed in vacuo
  2. customthe residue was chromatographed on silica in ethanol
  3. customto give an oil which
  4. customwas triturated with ether
  5. customrecrystallised from ethanol/ether
  6. customto give

출처 및 근거

ORD 기록
ord-357272ff030e41c1ab1609e5f6bd04f6
출처 데이터셋
uspto-grants-1989_09
특허 번호
US04863936

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