Hydrochloric Acid → 5-(((1-Methyl-5-oxo-1,2,3,5-tetrahydroimidazo[1,2-c]pyrimidin-7-yl)oxy)methyl)-2-(3-(trifluoromethyl)phenoxy)benzonitrile

HRID 873172Notes

Reaction equation

HRID 873172 reaction equation
[H-].[Na+].Cl[C:4]1[CH:5]=[C:6]2[N:13]([CH3:14])[CH2:12][CH2:11][N:7]2[C:8](=[O:10])[N:9]=1.[OH:15][CH2:16][C:17]1[CH:18]=[CH:19][C:20]([O:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:35])([F:34])[F:33])[CH:27]=2)=[C:21]([CH:24]=1)[C:22]#[N:23].Cl>CN(C=O)C>[CH3:14][N:13]1[C:6]2[N:7]([C:8](=[O:10])[N:9]=[C:4]([O:15][CH2:16][C:17]3[CH:18]=[CH:19][C:20]([O:25][C:26]4[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:33])([F:34])[F:35])[CH:27]=4)=[C:21]([CH:24]=3)[C:22]#[N:23])[CH:5]=2)[CH2:11][CH2:12]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 668254365-(Hydroxymethyl)-2-(3-(trifluoromethyl)phenoxy)benzonitrileHCID 717434587-Chloro-1-methyl-2,3-dihydroimidazo[1,2-C]pyrimidin-5(1H)-one

Product 1

HCID 712411455-(((1-Methyl-5-oxo-1,2,3,5-tetrahydroimidazo[1,2-c]pyrimidin-7-yl)oxy)methyl)-2-(3-(trifluoromethyl)phenoxy)benzonitrileYield 56.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

NaH (28.8 mg, 60%, 0.72 mmol) was added to a solution of 7-chloro-1-methyl-2,3-dihydroimidazo[1,2-c]pyrimidin-5(1H)-one (44 mg, 0.24 mmol) and 5-(hydroxymethyl)-2-(3-(trifluoromethyl)phenoxy)benzonitrile (71 mg, 0.242 mmol) in DMF (1.8 mL). The reaction mixture was stirred at rt for 30 min. Aqueous HCl solution was added to adjust pH to ˜7. Purification by Mass Directed AutoPrep (MDAP) afforded the title compound as a white solid (60 mg, 56% yield).

Workup

  1. customPurification by Mass Directed AutoPrep (MDAP)

Sources & evidence

ORD record
ord-850c2682af00421fa0855c247967ec9f
Source dataset
uspto-grants-2015_03
Patent number
US08975400B2

Reaction notes

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