Isopropanol → HCID 67125402, compound

HRID 1470761Notes

Reaction equation

HRID 1470761 reaction equation
[H-].[Na+].[CH3:3][CH:4]([OH:6])[CH3:5].Cl[C:8]1[N:13]=[CH:12][N:11]=[C:10]([N:14]2[CH2:19][CH2:18][CH:17]([C:20]3[CH:25]=[CH:24][C:23]([C@@H:26]([NH:28][C:29]([CH:31]4[CH2:33][CH2:32]4)=[O:30])[CH3:27])=[CH:22][CH:21]=3)[CH2:16][CH2:15]2)[CH:9]=1>O>[CH:4]([O:6][C:8]1[N:13]=[CH:12][N:11]=[C:10]([N:14]2[CH2:15][CH2:16][CH:17]([C:20]3[CH:21]=[CH:22][C:23]([C@@H:26]([NH:28][C:29]([CH:31]4[CH2:32][CH2:33]4)=[O:30])[CH3:27])=[CH:24][CH:25]=3)[CH2:18][CH2:19]2)[CH:9]=1)([CH3:5])[CH3:3]

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 24758Sodium hydrideHCID 87279052HCID 87279052, compound

Product 1

HCID 67125402HCID 67125402, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

25 mg (1.04 mmol) Sodium hydride are added to 2 mL 2-propanol and heated at 80° C. for 10 min. After that time, 80 mg (0.21 mmol) (S)-cyclopropanecarboxylic acid (1-{4-[1-(6-chloro-pyrimidin-4-yl)-piperidin-4-yl]-phenyl}-ethyl)-amide (XIV.6) are added. The mixture is heated at 80° C. for 12 h. After that time, water is added and the mixture is extracted with dichloromethane. The solvent is evaporated and the residue is purified using reversed phase HPLC (column: Waters XBridge 5 μM; eluent A: water+0.3% NH4OH, eluent B: MeOH) to yield the desired product.

Workup

  1. temperatureThe mixture is heated at 80° C. for 12 h
  2. extractionthe mixture is extracted with dichloromethane
  3. customThe solvent is evaporated
  4. customthe residue is purified

Sources & evidence

ORD record
ord-f7ec908cb2d94595ab9335ca3427887f
Source dataset
uspto-grants-2015_04
Patent number
US09006450B2

Reaction notes

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