2-Fluoroethylamine → HCID 90466849, compound

HRID 1753238Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([CH2:10][N:11]2[C:19]3[C:14](=[N:15][CH:16]=[C:17]([CH3:20])[CH:18]=3)[C:13]([C:21](O)=[O:22])=[CH:12]2)[C:5]([O:8][CH3:9])=[N:6][CH:7]=1.[F:24][CH2:25][CH2:26][NH2:27]>>[F:1][C:2]1[CH:3]=[C:4]([CH2:10][N:11]2[C:19]3[C:14](=[N:15][CH:16]=[C:17]([CH3:20])[CH:18]=3)[C:13]([C:21]([NH:27][CH2:26][CH2:25][F:24])=[O:22])=[CH:12]2)[C:5]([O:8][CH3:9])=[N:6][CH:7]=1

Participants

Reactant 2

HCID 99962-Fluoroethylamine

HCID 117818505HCID 117818505, compound

Product 1

HCID 90466849HCID 90466849, compound

Procedure

See FIG. 19(c). 1-((5-fluoro-2-methoxypyridin-3-yl)methyl)-6-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxylic acid (60 mg, 0.19 mmol) and 2-fluoroethanamine (21.60 mg, 0.34 mmol), TEA (0.080 mL, 0.57 mmol) was added. After 3 min1-Propanephosphonic acid cyclic anhydride (151 mg, 0.48 mmol) was added. The resulting reaction mixture was stirred at rt for 50 min. LCMS analysis showed 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 done on Waters RP system to get product 1-((5-fluoro-2-methoxypyridin-3-yl)methyl)-N-(2-fluoroethyl)-6-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide (25.00 mg, 36.5%). ES+MS m/z: 361.33. 1H NMR (300 MHz, DMSO-d6) δ ppm 2.44 (s, 3 H ) 3.65 (d, J=5.27 Hz, 1 H ) 3.75 (d, J=5.27 Hz, 1 H ) 3.90 (s, 3 H ) 4.49 (t, J=4.99 Hz, 1H ) 4.64 (t, J=4.99 Hz, 1 H ) 5.42 (s, 2 H ) 7.36 (dd, J=8.29, 3.01 Hz, 1 H ) 7.93 (s, 1H ) 8.12 (d, J=3.01 Hz, 1 H ) 8.23 (s, 1H ) 8.38 (s, 5 H ) 8.88 (t, J=5.65 Hz, 1 H ).

Workup

customThe resulting reaction mixture

Sources & evidence

ORD record: ord-e0f5cced4b22404092bcbbc6c5d9f2fd
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09163020B2

Reaction notes

Loading…