Diisopropylethylamine → HCID 58896782, compound

HRID 1409113Notes

Reaction equation

HRID 1409113 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4](F)[N:3]=1.Cl.[NH2:10][C@@H:11]([CH3:20])[C:12]([NH:14][CH2:15][C:16]([F:19])([F:18])[F:17])=[O:13].CCN(C(C)C)C(C)C>CN1C(=O)CCC1.C(OC(=O)C)C>[Br:1][C:2]1[N:3]=[C:4]([NH:10][C@@H:11]([CH3:20])[C:12]([NH:14][CH2:15][C:16]([F:17])([F:18])[F:19])=[O:13])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 6394382-Bromo-6-fluoropyridineHCID 56924314HCID 56924314, compound

Product 1

HCID 58896782HCID 58896782, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
220 °C

Procedure

A solution of 2-bromo-6-fluoropyridine (1.23 g, 7 mmol) and (S)-2-amino-N-(2,2,2-trifluoroethyl)propanamide hydrochloride (FF) (1.44 g, 7 mmol) in NMP (10 mL) was treated with DIPEA (2.4 mL, 14 mmol) and heated at 220° C. for 40 min in the microwave. After complete reaction, the mixture was diluted with ethylacetate (100 mL) then washed with water (5×25 mL), brine (1×25 mL) then dried over Na2SO4. The solvent was removed and the residue purified with silica-gel chromatography using hexane:ethyl acetate (4:1) to afford 1.5 g (66% yield) of a white solid, GG. LC-MS: 2.8 min, 327.8 ES+; 1H NMR (500 MHz, dmso-d6) d 8.56 (m, 1H), 7.29 (t, 1H), 7.13 (d, 1H), 6.68 (d, 1H), 6.55 (d, 1H), 4.36 (m, 1H), 3.90 (m, 2H), 1.30 (d, 3H).

Workup

  1. customAfter complete reaction
  2. washthen washed with water (5×25 mL), brine (1×25 mL)
  3. dry with materialthen dried over Na2SO4
  4. customThe solvent was removed
  5. customthe residue purified with silica-gel chromatography

Sources & evidence

ORD record
ord-84ea90d8daec4e19a3f4e8feb832d25f
Source dataset
uspto-grants-2014_12
Patent number
US08921376B2

Reaction notes

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