Cyclopropylamine → 4-Chloro-N-cyclopropylpyridine-2-carboxamide

HRID 626586Notes

Reaction equation

HRID 626586 reaction equation
[CH:1]1([NH2:4])[CH2:3][CH2:2]1.CCN(C(C)C)C(C)C.Cl.[Cl:15][C:16]1[CH:21]=[CH:20][N:19]=[C:18]([C:22](Cl)=[O:23])[CH:17]=1>C1COCC1.CCOC(C)=O>[Cl:15][C:16]1[CH:21]=[CH:20][N:19]=[C:18]([C:22]([NH:4][CH:1]2[CH2:3][CH2:2]2)=[O:23])[CH:17]=1

Participants

6

Reactant 3

HCID 69828CyclopropylamineHCID 81531DiisopropylethylamineHCID 223972704-Chloropyridine-2-carbonyl chloride--hydrogen chloride (1/1)

Product 1

HCID 256064754-Chloro-N-cyclopropylpyridine-2-carboxamideYield 116%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A 0° C. solution of cyclopropylamine (0.645 g, 11.30 mmol) and DIEA (1.973 mL, 11.30 mmol) in THF (15 mL) was treated with 4-chloropicolinoyl chloride hydrochloride (0.8 g, 3.77 mmol) in one portion, stirred at RT for 2 h, diluted with EtOAc and washed with satd. NaHCO3, then brine. The organic layer was dried over Na2SO4 and concentrated to dryness to afford 4-chloro-N-cyclopropylpicolinamide (0.86 g, 116%). 1H NMR (400 MHz, DMSO-d6): δ 8.83 (d, J=5.0 Hz, 1H), 8.58 (d, J=5.3 Hz, 1H), 7.99 (d, J=2.1 Hz, 1H), 7.74 (dd, J=5.3, 2.2 Hz, 1H), 2.89-2.88 (m, 1H), 0.68-0.66 (m, 4H); MS (ESI) m/z: 197.1 (M+H+).

Workup

  1. washwashed with satd
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-7d2ceb84a95741bebf3bed6587446e63
Source dataset
uspto-grants-2016_04
Patent number
US09309224B2

Reaction notes

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