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

HRID 1109994노트

반응식

HRID 1109994 반응식
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

참가 물질

7

반응물 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, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-b3b9b695650f4cf9a5d343f089e77cbf
출처 데이터셋
uspto-grants-1994_06
특허 번호
US05324724

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