4-Fluorobenzoic Acid → HCID 178523391, compound

HRID 1486480Notes

Reaction equation

HRID 1486480 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[C:7]2[O:12][C@H:13]1[CH2:18][CH2:17][C@H:16]([CH2:19][NH2:20])[CH2:15][CH2:14]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C.[F:54][C:55]1[CH:63]=[CH:62][C:58]([C:59](O)=[O:60])=[CH:57][CH:56]=1>O1CCCC1>[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[C:7]2[O:12][C@H:13]1[CH2:14][CH2:15][C@H:16]([CH2:19][NH:20][C:59](=[O:60])[C:58]2[CH:62]=[CH:63][C:55]([F:54])=[CH:56][CH:57]=2)[CH2:17][CH2:18]1

Participants

6

Reactant 4

HCID 99734-Fluorobenzoic AcidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178511283HCID 178511283, compound

Product 1

HCID 178523391HCID 178523391, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

{trans-4-[(8-Fluoroquinolin-4-yl)oxy]cyclohexyl}methylamine (1.82 g mg, 6.63 mmol) was dissolved in tetrahydrofuran (415 mL). After adding HATU (2.78 g, 7.30 mmol), diisopropylethylamine (1.30 mL, 7.30 mmol) and 4-fluorobenzoic acid (1.02 g, 7.30 mmol), the reaction mixture was stirred overnight at room temperature. After chromatography, the desired product was obtained at 71% yield (1.96 g).

Sources & evidence

ORD record
ord-688bf87b034d43a08620b2377acf64f3
Source dataset
uspto-grants-2016_08
Patent number
US09428460B2

Reaction notes

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