Ammonia → HCID 86682396, compound

HRID 1521749Notes

Reaction equation

HRID 1521749 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-N˜2˜-ethylpyridine-2,3-diamine (401 mg, 2.34 mmol) in ethanol (10 mL) is added a 3M solution of cyanogen bromide in CH2Cl2 (0.93 mL, 2.8 mmol) and the resulting 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 elution of 0-15% CH2Cl2/methanol containing 1% NH4OH to afford the title compound (212 mg, 46%).

Workup

  1. customevaporated
  2. customThe residue is purified via flash column chromatography
  3. washa gradient elution of 0-15% CH2Cl2/methanol containing 1% NH4OH

Sources & evidence

ORD record
ord-cb1fad4757844191a7355708cea06f7f
Source dataset
uspto-grants-2015_07
Patent number
US09073926B2

Reaction notes

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