Hydrochloric Acid → HCID 57489627, compound

HRID 2044074Notes

Reaction equation

HRID 2044074 reaction equation
[OH-].[Na+].Cl[C:4]1[N:12]=[C:11]([Cl:13])[CH:10]=[C:9]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]([N:23]3[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)=[O:22])=[CH:17][CH:16]=2)[C:5]=1[C:6]([NH2:8])=[O:7].Cl.[CH2:30]([OH:33])[CH2:31][CH3:32]>O>[Cl:13][C:11]1[CH:10]=[C:9]([NH:14][C:15]2[CH:16]=[CH:17][C:18]([C:21]([N:23]3[CH2:24][CH2:25][O:26][CH2:27][CH2:28]3)=[O:22])=[CH:19][CH:20]=2)[C:5]([C:6]([NH2:8])=[O:7])=[C:4]([O:33][CH2:30][CH2:31][CH3:32])[N:12]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10311-PropanolHCID 14798Sodium HydroxideHCID 57489626HCID 57489626, compound

Product 1

HCID 57489627HCID 57489627, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of powdered solid sodium hydroxide (121 mg, 3.04 mmol) in 1-propanol (10 mL) was stirred at rt until the solid material dissolved. Then 2,6-dichloro-4-(4-(morpholine-4-carbonyl)phenylamino)nicotinamide (600 mg, 1.518 mmol) was added and the mixture was stirred. The resulting suspension was placed in a heating block at 60° C. for 2 hrs. Next, the reaction mixture was cooled to rt and acidified with HCl (4 ml, 1N) and diluted with water. The cloudy precipitate was extracted into CH2Cl2 and concentrated to give 600 mg of light yellow solid. LCMS: (M+H)+=419.20, 421.19 (Cl pattern).

Workup

  1. dissolutiondissolved
  2. stirringthe mixture was stirred
  3. temperatureNext, the reaction mixture was cooled to rt
  4. extractionThe cloudy precipitate was extracted into CH2Cl2
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b824240a87e546b0a54a6b1c3d02414a
Source dataset
uspto-grants-2013_11
Patent number
US08586751B2

Reaction notes

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