4-Amino-3-fluorobenzoic acid → HCID 67159129, compound

HRID 2234439Notes

Reaction equation

[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[F:11].[CH3:12][N:13](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C[CH2:37][N:38]([CH:42]([CH3:44])[CH3:43])[CH:39]([CH3:41])[CH3:40].[CH3:45]C(N(C)C)=O>>[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:13][CH:12]2[CH2:41][C@H:39]3[N:38]([CH3:37])[C@H:42]([CH2:44][CH2:45][CH2:40]3)[CH2:43]2)=[O:8])=[CH:4][C:3]=1[F:11]

Participants

Reactant 4

HCID 99714-Amino-3-fluorobenzoic acid

HCID 31374Dimethylacetamide

HCID 81531Diisopropylethylamine

HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 67159129HCID 67159129, compound

Procedure

4-amino-3-fluorobenzoic acid (Fluorochem; 5.0 g, 32.2 mmol), HATU (13.5 g, 35.4 mmol) and DIPEA (18.5 mL, 106 mmol) were stirred together in anhydrous DMA (100 mL) for 25 minutes. Endo-9-methyl-9-azabicyclo[3,3,1]nonane-3-one (Chempacific; 5.5 g, 35.4 mmol) was added and the solution stirred at ambient temperature overnight.

Sources & evidence

ORD record: ord-2ea11f2b1ffe4447ad6efc4497282972
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07709471B2

Reaction notes

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