Ammonia → HCID 86682396, compound

HRID 1748322Notes

Reaction equation

HRID 1748322 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH3:10])[C:5]([NH2:11])=[CH:4][CH:3]=1.[N:12]#[C:13]Br.C(Cl)Cl.N>C(O)C.CO>[Cl:1][C:2]1[N:7]=[C:6]2[N:8]([CH2:9][CH3:10])[C:13]([NH2:12])=[N:11][C:5]2=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 6344DichloromethaneHCID 10476Cyanogen BromideHCID 10797271HCID 10797271, compound

Product 1

HCID 86682396HCID 86682396, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

To a solution of 6-chloro-N2-ethylpyridine-2,3-diamine (401 mg, 2.34 mmol) in ethanol (10 mL) is added a 3M solution of cyanogen bromide in DCM (0.93 mL, 2.8 mmol). The solution is stirred for 6 h at room temperature. The solution is basified with ammonia in methanol and evaporated. The residue is purified via flash column chromatography using a gradient of 0-15% methanol in CH2Cl2 containing 1% NH4OH to afford the title compound (212 mg, 46%).

Workup

  1. customevaporated
  2. customThe residue is purified via flash column chromatography

Sources & evidence

ORD record
ord-b81ac72ed6b34d968d2af90460f1d7b1
Source dataset
uspto-grants-2015_10
Patent number
US09150577B2

Reaction notes

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