Water → HCID 58554111, compound

HRID 1631014Notes

Reaction equation

HRID 1631014 reaction equation
F[C:2]1[C:9]([CH3:10])=[CH:8][C:5]([C:6]#[N:7])=[CH:4][N:3]=1.Cl.[C:12]([O:16][C:17](=[O:21])[CH2:18][CH2:19][NH2:20])([CH3:15])([CH3:14])[CH3:13].O>CS(C)=O>[C:6]([C:5]1[CH:8]=[C:9]([CH3:10])[C:2]([NH:20][CH2:19][CH2:18][C:17]([O:16][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:21])=[N:3][CH:4]=1)#[N:7]

Participants

5

Reactant 3

HCID 962WaterHCID 16218890Tert-butyl 3-aminopropanoate hydrochlorideHCID 232882695-Cyano-2-fluoro-3-picoline

Product 1

HCID 58554111HCID 58554111, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 6-fluoro-5-methylnicotinonitrile (Molekula 11370, 10 g, 73.4 mmol), beta-alanine tert-butyl ester hydrochloride (16 g, 88.1 mmol) and TEA (25.6 mL, 183.6 mmol) was prepared in DMSO (100 mL) under nitrogen, and then heated at 150° C. for 4 hours. The reaction mixture was cooled to 100° C. and water (100 mL) was added drop wise. The resulting mixture was stirred at RT for 2 hours, and then the precipitate was filtered off, washed with water and dried under reduced pressure to afford the title compound as a white solid (18 g, 94%). 1H NMR (DMSO-d6, 400 MHz) δ 8.31 (1H, s), 7.56 (1H, s), 6.97 (1H, m), 3.59 (2H, m), 2.50 (2H, m), 2.02 (3H, s), 1.36 (9H, s).

Workup

  1. temperatureThe reaction mixture was cooled to 100° C.
  2. filtrationthe precipitate was filtered off
  3. washwashed with water
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-db5d696003c5405fad302b961f1d6b07
Source dataset
uspto-grants-2014_07
Patent number
US08791142B2

Reaction notes

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