2-Fluoroethylamine → HCID 72792633, compound

HRID 1753232Notes

Reaction equation

[CH3:1][O:2][C:3]1[N:8]=[CH:7][N:6]=[C:5]([CH2:9][N:10]2[C:18]3[C:13](=[N:14][CH:15]=[C:16]([CH3:19])[CH:17]=3)[C:12]([C:20]([OH:22])=O)=[CH:11]2)[C:4]=1[CH3:23].[F:24][CH2:25][CH2:26][NH2:27]>>[F:24][CH2:25][CH2:26][NH:27][C:20]([C:12]1[C:13]2=[N:14][CH:15]=[C:16]([CH3:19])[CH:17]=[C:18]2[N:10]([CH2:9][C:5]2[C:4]([CH3:23])=[C:3]([O:2][CH3:1])[N:8]=[CH:7][N:6]=2)[CH:11]=1)=[O:22]

Participants

Reactant 2

HCID 99962-Fluoroethylamine

HCID 117819025HCID 117819025, compound

Product 1

HCID 72792633HCID 72792633, compound

Procedure

See FIG. 17(d). 1-((6-methoxy-5-methylpyrimidin-4-yl)methyl)-6-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxylic acid (0.190 gm, 0.61 mmol) and 2-fluoroethanamine (0.077 g. 1.22 mmol), TEA (0.254 mL, 1.83 mmol) was added. After 3 min1-Propanephosphonic acid cyclic anhydride (0.484 g, 1.52 mmol) was added. The resulting reaction mixture was stirred at rt for 50 min. LCMS analysis confirmed the formation of required product. Reaction was diluted with DCM and water.DCM layer was extracted and washed with brine and dried over sodium sulphate and concentrated. Purification was performed on Waters RP system to get product N-(2-fluoroethyl)-1-((6-methoxy-5-methylpyrimidin-4-yl)methyl)-6-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide (0.090 g, 41.4%). ES+MS m/z: 358.36. 1H NMR (300 MHz, DMSO-d6) δ ppm 2.17-2.30 (3, 3 H) 2.40 (s, 3 H ) 3.59-3.73 (m, 1 H ) 3.73-3.83 (m, 1 H ) 3.94 (s, 3 H ) 4.50 (t, J=4.99 Hz, 1 H ) 4.66 (t, J=4.99 Hz, 1 H ) 5.64 (s, 2 H ) 7.76 (s, 1 H ) 8.15 (s, 1 H ) 8.35 (s, 1 H ) 8.42 (s, 1 H ) 8.87 (t, J=5.84 Hz, 1 H ).

Workup

customThe resulting reaction mixture

Sources & evidence

ORD record: ord-ff2d765f96f34c368b97333ac8fe3139
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09163020B2

Reaction notes

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