Hydrochloric Acid → HCID 11201639, compound

HRID 2217887Notes

Reaction equation

HRID 2217887 reaction equation
C([O:3][C:4](=[O:33])[CH2:5][NH:6][C@H:7]1[CH2:11][CH2:10][N:9]([C:12]2[CH:21]=[CH:20][C:19]3[C:14](=[CH:15][CH:16]=[C:17]([Cl:32])[C:18]=3[NH:22][C:23](=[O:31])[CH2:24][CH:25]3[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)[N:13]=2)[CH2:8]1)C.[OH-].[Na+].Cl>CO>[Cl:32][C:17]1[C:18]([NH:22][C:23](=[O:31])[CH2:24][CH:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)=[C:19]2[C:14](=[CH:15][CH:16]=1)[N:13]=[C:12]([N:9]1[CH2:10][CH2:11][C@H:7]([NH:6][CH2:5][C:4]([OH:33])=[O:3])[CH2:8]1)[CH:21]=[CH:20]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 68811261HCID 68811261, compound

Product 1

HCID 11201639HCID 11201639, compoundYield 29.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-[(3S)-1-[6-Chloro-5-[(cyclohexylacetyl)amino]-2-quinolinyl]-3-pyrrolidinyl]-glycine ethyl ester (Example 85(a)) (100 mg), 1M sodium hydroxide (0.422 mL) and methanol (5 mL) were stirred for 12 hours before reaction was acidified with 1M hydrochloric acid and volatiles removed under vacuum. Purification (SiO2, 7M ammonia in methanol:methanol:dichloromethane 1:4:95) gave the title compound (0.028 g)

Workup

  1. customremoved under vacuum
  2. customPurification (SiO2, 7M ammonia in methanol:methanol:dichloromethane 1:4:95)

Sources & evidence

ORD record
ord-1c97406bce83440abc9d47f227e419af
Source dataset
uspto-grants-2008_08
Patent number
US07408065B2

Reaction notes

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