Dimethylformamide → HCID 57960989, compound

HRID 449072Notes

Reaction equation

[NH2:1][C:2]1[C:3]2[N:4]([CH:8]([CH:18]3[CH2:21][CH2:20][CH2:19]3)[N:9](C3C=CC(O)=CC=3)[CH:10]=2)[CH:5]=[CH:6][N:7]=1.[C:22](=[O:25])([O-])[O-].[K+].[K+].CN(C=O)C.[C:33](#[N:40])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>>[NH2:1][C:2]1[C:3]2[N:4]([C:8]([CH:18]3[CH2:19][CH2:20][CH2:21]3)=[N:9][C:10]=2[C:19]2[CH:20]=[CH:21][C:22]([O:25][C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=3[C:33]#[N:40])=[CH:8][CH:18]=2)[CH:5]=[CH:6][N:7]=1

Participants

Reactant 4

HCID 6228Dimethylformamide

HCID 7505Benzonitrile

HCID 11430Potassium Carbonate

HCID 66915468HCID 66915468, compound

Product 1

HCID 57960989HCID 57960989, compound

Conditions

Temperature: 120 °C

Procedure

Into a 10 mL round bottom flask was added 4-(8-amino-3-cyclobutylimidazo[1,5-a]pyrazin-2-yl)phenol (20 mg, 0.00007 mol), benzonitrile, 2-fluoro-(0.017 g, 0.00014 mol), potassium carbonate (0.015 g, 0.00011 mol), DMF (0.6 mL, 0.007 mol) and the reaction was heated at 120° C. for 4 h. Purification by Gilson HPLC afforded 5.0 mg of the title compound as a white solid. The compound was passed through an SPE cartridge washing with NH3 in MeOH to elute 4.8 my of the desired compound free of the TFA salt. MS(ES+): m/z 381.93 (100)[MH+]. HPLC: tR=2.39 min (Open Lynx polar—5 min).

Workup

customPurification by Gilson HPLC

Sources & evidence

ORD record: ord-49d345fde0404634b3b8a2e1ad35ee88
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08481733B2

Reaction notes

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