Piperidine → HCID 57489634, compound

HRID 2044085Notes

Reaction equation

HRID 2044085 reaction equation
Cl[C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[C:4]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([S:18]([CH3:21])(=[O:20])=[O:19])=[CH:14][CH:13]=2)[N:3]=1.[NH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1>CCOC(C)=O>[CH3:21][S:18]([C:15]1[CH:16]=[CH:17][C:12]([NH:11][C:4]2[N:3]=[C:2]([N:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)[CH:10]=[CH:9][C:5]=2[C:6]([NH2:8])=[O:7])=[CH:13][CH:14]=1)(=[O:20])=[O:19]

Participants

4

Reactant 2

HCID 8082PiperidineHCID 57489636HCID 57489636, compound

Product 1

HCID 57489634HCID 57489634, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 6-chloro-2-(4-(methylsulfonyl)phenylamino)nicotinamide (19.4 mg, 0.060 mmol) and piperidine (2 mL) in a sealed tube was stirred in a 90° C. oil bath for 5 h. The mixture was diluted with EtOAc (25 mL), washed with saturated NH4Cl(2×5 mL), brine (5 mL), dried (MgSO4), and concentrated. After addition of CH2Cl2 (2 mL), white solid precipitated from the solution upon sitting. The solid was collected by filtration (14.1 mg, 60%). LCMS: (M+H)+=375.1. 1H NMR (400 MHz, acetone-d6) δ ppm 12.20 (1H, s), 7.90-8.09 (3H, m), 7.78-7.89 (2H, m), 6.33 (1H, d, J=8.78 Hz), 3.58-3.89 (4H, m), 3.07 (3H, s), 1.52-1.85 (6H, m).

Workup

  1. washwashed with saturated NH4Cl(2×5 mL), brine (5 mL)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. additionAfter addition of CH2Cl2 (2 mL), white solid
  5. customprecipitated from the solution
  6. filtrationThe solid was collected by filtration (14.1 mg, 60%)

Sources & evidence

ORD record
ord-1e156e517cba4c3c808eb0a17c4fca1c
Source dataset
uspto-grants-2013_11
Patent number
US08586751B2

Reaction notes

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