Acetonitrile → HCID 68089119, compound

HRID 539767Notes

Reaction equation

C(#N)C.[CH2:4]([O:6][C:7]1[CH:12]=[CH:11][C:10]2=[N:13][C:14]([C:16]3[CH:17]=[CH:18][C:19]([C:25]([F:28])([F:27])[F:26])=[C:20]([CH:24]=3)[C:21](O)=[O:22])=[CH:15][N:9]2[N:8]=1)[CH3:5].[C:29]([NH2:33])([CH3:32])([CH3:31])[CH3:30].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>C(N(CC)CC)C>[C:29]([NH:33][C:21](=[O:22])[C:20]1[CH:24]=[C:16]([C:14]2[N:13]=[C:10]3[N:9]([CH:15]=2)[N:8]=[C:7]([O:6][CH2:4][CH3:5])[CH:12]=[CH:11]3)[CH:17]=[CH:18][C:19]=1[C:25]([F:27])([F:28])[F:26])([CH3:32])([CH3:31])[CH3:30]

Participants

Conditions

Temperature: 80 °C

Procedure

An 8 mL vial is charged with acetonitrile (0.5 mL), 5-(6-ethoxyimidazo[2,1-f]pyridazin-2-yl)-2-(trifluoromethyl)benzoic acid (0.035 g, 0.0001 mol), tert-butylamine (0.016 mL), triethylamine (0.055 mL), and (benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (0.088 g). The mixture is stirred and heated at 80° C. for 16 hr, cooled, concentrated onto celite and purified by silica (0-100% EtOAc in Hexanes) to give the title compound (0.011 g, 28% yield). LCMS m/z=407.5 [M+H]+, tR=2.74 min. (compound same as Example 211)

Workup

temperaturecooled
concentrationconcentrated onto celite
custompurified by silica (0-100% EtOAc in Hexanes)

Sources & evidence

ORD record: ord-48e034b6cf7e4ab6a410dc800cb1dd56
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871767B2

Reaction notes

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