Hydrochloric Acid → 4-(3-Amino-1,2,4-triazin-5-yl)-1-azabicyclo[2.2.1]heptane

HRID 1109994ノート

反応式

HRID 1109994 の反応式
Br.Br[CH2:3][C:4]([C:6]12[CH2:12][N:9]([CH2:10][CH2:11]1)[CH2:8][CH2:7]2)=O.Br.O=C(C12CN(CC1)CC2)C=O.C(=O)(O)O.[NH2:29][NH:30][C:31]([NH2:33])=[NH:32].Cl.C(=O)([O-])[O-].[K+].[K+]>O>[NH2:33][C:31]1[N:30]=[N:29][CH:3]=[C:4]([C:6]23[CH2:12][N:9]([CH2:10][CH2:11]2)[CH2:8][CH2:7]3)[N:32]=1

参加物

7

反応物 5

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 190185941-(1-Azabicyclo[2.2.1]heptan-4-yl)-2-bromoethanone;hydrobromideHCID 867479402-Oxo-2-(1-azabicyclo[2.2.1]hept-4-yl) ethanal hydrobromideHCID 178513185HCID 178513185、化合物

生成物 1

HCID 190186004-(3-Amino-1,2,4-triazin-5-yl)-1-azabicyclo[2.2.1]heptane収率 43.8%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

4-(α-bromoacetyl) -1 -azabicyclo[2.2.1 ]heptane hydrobromide (EP-0366304, Description 19) (0.5 g, 1.67 mmol) was converted into 2-oxo-2- (1-azabicyclo [2.2.1]hept-4-yl)ethanal hydrobromide as described in Example 3. The crude aldehyde was immediately treated with a suspension of aminoguanidine bicarbonate (0.25 g, 1.84 mmol) in water (10 ml) and the solution was acidified to pH6 with 5M hydrochloric acid. After stirring overnight at room temperature the reaction mixture was saturated with potassium carbonate then extracted into chloroform (4×20 ml). The combined organic extracts were dried over sodium sulphate and concentrated in vacuo. The residue was crystallised from isopropanolpentane to afford the title compound (E4) as a brown solid (0.14 g, 43%) . This was converted into the oxalate salt m.p. 178° C. (dec) (from methanol-ether).

後処理

  1. extractionthen extracted into chloroform (4×20 ml)
  2. dry with materialThe combined organic extracts were dried over sodium sulphate
  3. concentrationconcentrated in vacuo
  4. customThe residue was crystallised from isopropanolpentane

出典と根拠

ORDレコード
ord-b3b9b695650f4cf9a5d343f089e77cbf
出典データセット
uspto-grants-1994_06
特許番号
US05324724

反応ノート

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