Carbonic acid-guanidine (1:1) → HCID 11703778, compound

HRID 2176990Notes

Reaction equation

HRID 2176990 reaction equation
C(=O)(O)O.[NH2:5][C:6]([NH2:8])=[NH:7].[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([CH:16]([CH2:28][O:29][CH2:30][O:31][CH3:32])[CH2:17][O:18][C:19]2[CH:26]=[CH:25][CH:24]=[C:23](F)[C:20]=2[C:21]#[N:22])=[CH:12][CH:11]=1>CC(N(C)C)=O>[Cl:9][C:10]1[CH:11]=[CH:12][C:13]([CH:16]([CH2:28][O:29][CH2:30][O:31][CH3:32])[CH2:17][O:18][C:19]2[CH:26]=[CH:25][CH:24]=[C:23]3[C:20]=2[C:21]([NH2:22])=[N:7][C:6]([NH2:8])=[N:5]3)=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 286947Carbonic acid-guanidine (1:1)HCID 66924160HCID 66924160, compound

Product 1

HCID 11703778HCID 11703778, compoundYield 24.4%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
135 °C

Procedure

Guanidine carbonate (792 mg; 4.4 mmol) is suspended in a solution of 2-[2-(4-Chlorophenyl)-3-methoxymethoxypropoxy]-6-fluorobenzonitrile (769 mg; 2.20 mmol) in DMA, and heated to 135° C. for 8 hours. The solution is cooled to RT overnight and placed in a freezer at 4° C. for 24 hours. The resulting black solids are removed by filtration through paper. The filtrate is concentrated under vacuum, and purified by column chromatography (10% MeOH/EtOAc). The collected fractions are dried to give 209 milligrams of 5-[2-(4-chlorophenyl)-3-methoxymethoxy propoxy]-quinazoline-2,4-diamine.

Workup

  1. temperatureThe solution is cooled to RT overnight
  2. customThe resulting black solids are removed by filtration through paper
  3. concentrationThe filtrate is concentrated under vacuum
  4. custompurified by column chromatography (10% MeOH/EtOAc)
  5. customThe collected fractions are dried

Sources & evidence

ORD record
ord-b2147532edfe42938eefa6cc87c39923
Source dataset
uspto-grants-2015_06
Patent number
US09067897B2

Reaction notes

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