Nitromethane → HCID 86667445, compound

HRID 75010Notes

Reaction equation

HRID 75010 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C@H:9]2[CH2:14][CH2:13][CH2:12][C:11](=[CH:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:10]2)[C:5]([F:21])=[CH:4][N:3]=1.[N+:22]([CH3:25])([O-:24])=[O:23].CN(C)C(N(C)C)=N>>[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C@H:9]2[CH2:14][CH2:13][CH2:12][C:11]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])([CH2:25][N+:22]([O-:24])=[O:23])[CH2:10]2)[C:5]([F:21])=[CH:4][N:3]=1

Participants

4

Reactant 3

HCID 6375NitromethaneHCID 664601,1,3,3-TetramethylguanidineHCID 86667443HCID 86667443, compound2×

Product 1

HCID 86667445HCID 86667445, compound

Procedure

To a solution of (5)-ethyl 2-(3-(2-chloro-5-fluoropyrimidin-4-ylamino)cyclohexylidene)ethanoate, 62a, (2.58 g, 8.22 mmol) in nitromethane (44.53 mL, 822.3 mmol) was added 1,1,3,3-tetramethylguanidine (1.55 mL, 12.33 mmol). The reaction was refluxed overnight then concentrated in vacuo and purified by silica gel chromatography (Hexanes:EtOAc) then a second chromatography (CH2Cl2:20% MeOH in CH2Cl2). Fractions containing pure product were combined and concentrated to give 1.8 g of 62b

Workup

  1. temperatureThe reaction was refluxed overnight
  2. concentrationthen concentrated in vacuo
  3. custompurified by silica gel chromatography (Hexanes:EtOAc)
  4. additionFractions containing pure product
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9ec97526996a41e4b8b991e63ecd759e
Source dataset
uspto-grants-2014_09
Patent number
US08829007B2

Reaction notes

Loading…