Carbonic acid-guanidine (1:1) → HCID 25003845, compound

HRID 1015372Notes

Reaction equation

HRID 1015372 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][O:15][C:16]2[CH:23]=[CH:22][CH:21]=[C:20](F)[C:17]=2[C:18]#[N:19])[CH2:10][CH2:9]1.C(=O)(O)O.[NH2:29][C:30]([NH2:32])=[NH:31]>CC(N(C)C)=O.O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH2:9][CH2:10][CH:11]([CH2:14][O:15][C:16]2[CH:23]=[CH:22][CH:21]=[C:20]3[C:17]=2[C:18]([NH2:19])=[N:31][C:30]([NH2:32])=[N:29]3)[CH2:12][CH2:13]1

Participants

5

Reactant 2

HCID 286947Carbonic acid-guanidine (1:1)HCID 67301343HCID 67301343, compound

Product 1

HCID 25003845HCID 25003845, compoundYield 29%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Procedure

2-[1-(2-Chlorophenyl)piperidin-4-ylmethoxy]-6-fluorobenzonitrile (0.28 g; 0.81 mmol) and guanidine carbonate (0.293 mg; 1.6 mmol) were heated at 140° C. in dimethylacetamide for 2 days, then cooled back to room temperature. The reaction mixture was diluted with water, stirred for 45 minutes, filtered, triturated with ethanol, and filtered. Solids were dried to afford 90 milligrams of 5-[1-(2-chlorophenyl)-piperidin-4-ylmethoxy)quinazoline-2,4-diamine (29% yield).

Workup

  1. filtrationfiltered
  2. customtriturated with ethanol
  3. filtrationfiltered
  4. customSolids were dried

Sources & evidence

ORD record
ord-0061d84bec874e95a21fca71be8ea5e7
Source dataset
uspto-grants-2011_07
Patent number
US07985755B2

Reaction notes

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