HCID 12448337, compound → HCID 178512061, compound

HRID 2117395Notes

Reaction equation

HRID 2117395 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][CH2:8][CH2:7][CH:6]2[NH2:11])[O:4][CH2:3][CH2:2]1.[Cl:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[C:14]=1[NH:20][C:21]#[N:22]>>[Cl:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[C:14]=1[NH:20][C:21]([NH:11][CH:6]1[CH2:7][CH2:8][CH2:9][CH2:10][C:5]21[O:4][CH2:3][CH2:2][O:1]2)=[NH:22]

Participants

3

Reactant 2

HCID 12448337HCID 12448337, compoundHCID 22139851HCID 22139851, compound

Product 1

HCID 178512061HCID 178512061, compoundYield 43.5%

Procedure

1,4-Dioxaspiro[4.5]dec-6-ylamine (500 mg) was reacted with 2,6-dichloro-phenylcyanamide (595 mg, prepared as described in J. Med. Chem., 1975, 18, 90-99) at 130° C. After 45 minutes, the reaction was stopped and the reaction product was purified by preparative HPLC. The product-containing fractions were combined, the acetonitrile was stripped off in a rotary evaporator, and the aqueous residue was neutralized with potassium carbonate and extracted three times with dichloromethane. Drying over magnesium sulfate was followed by evaporation to dryness. 476 mg of the desired guanidine were obtained.

Workup

  1. customthe reaction product was purified by preparative HPLC
  2. customthe acetonitrile was stripped off in a rotary evaporator
  3. extractionextracted three times with dichloromethane
  4. dry with materialDrying over magnesium sulfate
  5. customwas followed by evaporation to dryness

Sources & evidence

ORD record
ord-6c6461ddd418478096aad7814b6e4525
Source dataset
uspto-grants-2008_10
Patent number
US07442717B2

Reaction notes

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