Guanidine Hydrochloride → HCID 9814006, compound

HRID 747481Notes

Reaction equation

[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](=O)[CH2:7][C:8]1[CH:9]=[CH:10][C:11](=[O:15])[N:12]([CH3:14])[CH:13]=1.[CH3:17]OC(OC)N(C)C.Cl.[NH2:26][C:27]([NH2:29])=[NH:28].N12CCCN=C1CCCCC2>CC(O)C.CN(C)C=O>[NH2:28][C:27]1[N:29]=[C:6]([C:2]2[O:1][CH:5]=[CH:4][CH:3]=2)[C:7]([C:8]2[CH:9]=[CH:10][C:11](=[O:15])[N:12]([CH3:14])[CH:13]=2)=[CH:17][N:26]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To 5-(2-furan-2-yl-2-oxo-ethyl)-1-methyl-1H-pyridin-2-one (8) (402.0 g, content 397.6 g, 1.83 mol) obtained in Preparation Example 5 were added dimethylformamide (0.4 L) and N,N-dimethylformamide dimethyl acetal (654.4 g, 5.49 mol), and the reaction mixture was stirred at 60° C. for 10.5 hours and then at room temperature for 13.5 hours. To the reaction mixture were added guanidine hydrochloride (524.56 g, 5.49 mol) and 1,8-diazabicyclo[5.4.0]undec-7-en (DBU) (821 mL, 5.49 mol), and the reaction mixture was stirred for 7.8 hours at 70° C. Next, to the reaction mixture was added 2-propanol (12.0 L), followed by stirring for 2 hours in an ice bath. The precipitated crystals were collected by filtration, washed with 2-propanol (1.0 L), and then air-dried at 60° C. for 13 hours to give 424.9 g of the title compound as pale yellow crystals (content 413.0 g, yield 84.1%).

Workup

waitat room temperature for 13.5 hours
stirringthe reaction mixture was stirred for 7.8 hours at 70° C
stirringby stirring for 2 hours in an ice bath
filtrationThe precipitated crystals were collected by filtration
washwashed with 2-propanol (1.0 L)
customair-dried at 60° C. for 13 hours

Sources & evidence

ORD record: ord-a6f1b5cf9e32433392ad8a5418c68a2a
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07396928B2

Reaction notes

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