Hydrochloric Acid → HCID 68580003, compound

HRID 2234022Notes

Reaction equation

HRID 2234022 reaction equation
O.[OH-].[Na+].[Cl:4][C:5]1[C:9]([Cl:10])=[C:8]([CH3:11])[NH:7][C:6]=1[C:12]([NH:14][CH:15]1[CH2:20][CH2:19][N:18]([C:21]2[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH:24]=[C:23]([C:31]([O:33]C)=[O:32])[N:22]=2)[CH2:17][CH2:16]1)=[O:13].Cl>C1COCC1.CCOC(C)=O>[Cl:4][C:5]1[C:9]([Cl:10])=[C:8]([CH3:11])[NH:7][C:6]=1[C:12]([NH:14][CH:15]1[CH2:16][CH2:17][N:18]([C:21]2[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH:24]=[C:23]([C:31]([OH:33])=[O:32])[N:22]=2)[CH2:19][CH2:20]1)=[O:13]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 68579750methyl 1-(4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)isoquinoline-3-carboxylate

Product 1

HCID 68580003HCID 68580003, compoundYield 73.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
80 °C

Procedure

In a mixture of 20 ml THF, 5 ml H2O, and 1 ml 50 wt % NaOH (aq) was dissolved methyl 1-(4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)isoquinoline-3-carboxylate (Example 301; 70 mg). The solution was stirred at 80° C. for 1 hr. The solution was cooled to room temperature, diluted with EtOAc and acidified with dilute HCl (aq). The EtOAc fraction was isolated, at which time a white solid precipitated from solution. The solid was collected by filtration and washed with acetonitrile to yield 50 mg white solid product.

Workup

  1. temperatureThe solution was cooled to room temperature
  2. customprecipitated from solution
  3. filtrationThe solid was collected by filtration
  4. washwashed with acetonitrile

Sources & evidence

ORD record
ord-459a067e62e14c9baed96479d30ec4dc
Source dataset
uspto-grants-2010_05
Patent number
US07709503B2

Reaction notes

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