Hydrochloric Acid → HCID 57377892, compound

HRID 72544Notes

Reaction equation

HRID 72544 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5]([N:24]2[CH2:28][CH2:27][CH2:26][CH:25]2[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[C:6]([CH:23]=1)[C:7]([NH:9][C:10]1([C:13]2[CH:22]=[CH:21][C:16]([C:17]([O:19]C)=[O:18])=[CH:15][CH:14]=2)[CH2:12][CH2:11]1)=[O:8].[OH-].[Na+].Cl>CO.O1CCCC1>[Cl:1][C:2]1[CH:3]=[N:4][C:5]([N:24]2[CH2:28][CH2:27][CH2:26][CH:25]2[C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)=[C:6]([CH:23]=1)[C:7]([NH:9][C:10]1([C:13]2[CH:14]=[CH:15][C:16]([C:17]([OH:19])=[O:18])=[CH:21][CH:22]=2)[CH2:12][CH2:11]1)=[O:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67958454Methyl 4-(1-(5-chloro-2-(2-phenylpyrrolidin-1-yl)nicotinamido)cyclopropyl)benzoate

Product 1

HCID 57377892HCID 57377892, compoundYield 60.6%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

To an ice cooled solution of methyl 4-(1-(5-chloro-2-(2-phenylpyrrolidin-1-yl)nicotinamido)cyclopropyl)benzoate (D142) (189 mg, 0.40 mmol). in a mixture methanol/tetrahydrofuran (10 ml/10 ml), 2N NaOH (10 ml) was added. The reaction mixture was heated to 40° C. for 2 hours then cooled to 0° C., acidified with 2.5N HCl (pH=1-2) and stirred at 0° C. for 10 min. The formed solid was collected by filtration and dried to provide title compound (E1) (112 mg).

Workup

  1. temperaturethen cooled to 0° C.
  2. filtrationThe formed solid was collected by filtration
  3. customdried

Sources & evidence

ORD record
ord-b4ed009f820244d6826e744cd76aeb6f
Source dataset
uspto-grants-2014_09
Patent number
US08828987B2

Reaction notes

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