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

HRID 1607064ノート

反応式

HRID 1607064 の反応式
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

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒2 回HCID 6212Chloroform溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-357272ff030e41c1ab1609e5f6bd04f6
出典データセット
uspto-grants-1989_09
特許番号
US04863936

反応ノート

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