2-Methoxyethylamine → HCID 118036934, compound

HRID 1778035Notes

Reaction equation

HRID 1778035 reaction equation
[C:1]([O:5][C:6](=[O:17])[NH:7][C:8]1[CH:13]=[C:12](Cl)[C:11]([C:15]#[N:16])=[CH:10][N:9]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:18][O:19][CH2:20][CH2:21][NH2:22].CCN(C(C)C)C(C)C>CS(C)=O>[C:1]([O:5][C:6](=[O:17])[NH:7][C:8]1[CH:13]=[C:12]([NH:22][CH2:21][CH2:20][O:19][CH3:18])[C:11]([C:15]#[N:16])=[CH:10][N:9]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 80182-MethoxyethylamineHCID 81531DiisopropylethylamineHCID 127255428HCID 127255428, compound2×

Product 1

HCID 118036934HCID 118036934, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
67.5 °C

Procedure

A mixture of tert-butyl(4-chloro-5-cyanopyridin-2-yl)carbamate (intermediate 288, 9.8 g, 38.6 mmol), 2-methoxyethylamine (5.8 g, 77.3 mmol) and DIPEA (6 g, 46.4 mmol) in DMSO (80 ml) was heated at 65-70° C. for 24 h and monitored by chromatography until complete conversion. The solution was then cooled to room temperature and a white solid precipitated gradually. Water (20 ml) was then added slowly within 1 h. The suspension was stirred for a further 1 h, filtered and dried to give the title compound as a white solid. 1H NMR (DMSO-d6, 400 MHz): δ 9.87 (s, 1H), 8.18 (s, 1H), 7.20 (s, 1H), 6.86 (s, 9H), 3.51 (t, 2H), 3.36 (t, 2H), 3.28 (s, 3H), 1.47 (s, 9H).

Workup

  1. temperatureThe solution was then cooled to room temperature
  2. customa white solid precipitated gradually
  3. additionWater (20 ml) was then added slowly within 1 h
  4. filtrationfiltered
  5. customdried

Sources & evidence

ORD record
ord-e728c78c320e44d08b9b4176541c105f
Source dataset
uspto-grants-2016_02
Patent number
US09266883B2

Reaction notes

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