Guanidine Hydrochloride → HCID 178513082, compound

HRID 488803Notes

Reaction equation

HRID 488803 reaction equation
Cl.[NH2:2][C:3]([NH2:5])=[NH:4].C[O-:7].[Na+].[N:9]1[C:18]2[C:13](=[C:14]([N:19]3[C:23]([CH:24]4[CH2:26][CH2:25]4)=[C:22]([C:27]([O:29]CC)=[O:28])[CH:21]=[N:20]3)[CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][CH:10]=1>C(O)C>[OH2:28].[OH2:7].[N:9]1[C:18]2[C:13](=[C:14]([N:19]3[C:23]([CH:24]4[CH2:25][CH2:26]4)=[C:22]([C:27]([NH:4][C:3]([NH2:5])=[NH:2])=[O:29])[CH:21]=[N:20]3)[CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 5742Guanidine HydrochlorideHCID 10942334Sodium MethoxideHCID 22267584HCID 22267584, compound

Product 1

HCID 178513082HCID 178513082, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of guanidine hydrochloride (3.11 g, 32.6 mmol) in warm anhydrous ethanol (8 mL) under a nitrogen atmosphere was treated in one portion with sodium methoxide (1.76 g, 32.6 mmol). The resulting slurry was concentrated in vacuo. The residue was treated with anhydrous toluene (10 mL) and concentrated to dryness in vacuo (twice). Each time the vacuum was released to a nitrogen atmosphere. The residue was treated in one portion with ethyl 1-(quinolin-5-yl)-5-cyclopropyl-1H-pyrazole-4-carboxylate (1.00 g, 3.26 mmol) in anhydrous ethanol (8 mL). The resulting mixture was concentrated in vacuo (rotatory evaporator, 80° C. water bath). The residue was treated with anhydrous toluene (10 mL) and the resulting mixture was concentrated in vacuo (three times). The resulting solid was triturated with water (85 mL) and filtered. The solid was air-dried to provide 0.880 g (76% yield) of [1-(quinolin-5-yl)-5-cyclopropyl-1H-pyrazole-4-carbonyl]guanidine dihydrate.

Workup

  1. concentrationThe resulting slurry was concentrated in vacuo
  2. additionThe residue was treated with anhydrous toluene (10 mL)
  3. concentrationconcentrated to dryness in vacuo (twice)
  4. concentrationThe resulting mixture was concentrated in vacuo (rotatory evaporator, 80° C. water bath)
  5. additionThe residue was treated with anhydrous toluene (10 mL)
  6. concentrationthe resulting mixture was concentrated in vacuo (three times)
  7. customThe resulting solid was triturated with water (85 mL)
  8. filtrationfiltered
  9. customThe solid was air-dried

Sources & evidence

ORD record
ord-f962a5f3330041e797bb42b55496d47b
Source dataset
uspto-grants-2005_12
Patent number
US06974813B2

Reaction notes

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