Hydrochloric Acid → 2-({4-[({6-[Cyclohexyl(cyclopropylmethyl)amino]pyrimidin-4-yl}carbonyl)amino]benzyl}amino)butanoic acid

HRID 1946773Notes

Reaction equation

HRID 1946773 reaction equation
[CH:1]1([N:7]([CH2:32][CH:33]2[CH2:35][CH2:34]2)[C:8]2[N:13]=[CH:12][N:11]=[C:10]([C:14]([NH:16][C:17]3[CH:31]=[CH:30][C:20]([CH2:21][NH:22][CH:23]([CH2:28][CH3:29])[C:24]([O:26]C)=[O:25])=[CH:19][CH:18]=3)=[O:15])[CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+].Cl>CO.C1COCC1>[CH:1]1([N:7]([CH2:32][CH:33]2[CH2:34][CH2:35]2)[C:8]2[N:13]=[CH:12][N:11]=[C:10]([C:14]([NH:16][C:17]3[CH:18]=[CH:19][C:20]([CH2:21][NH:22][CH:23]([CH2:28][CH3:29])[C:24]([OH:26])=[O:25])=[CH:30][CH:31]=3)=[O:15])[CH:9]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59446901Methyl 2-({4-[({6-[cyclohexyl(cyclopropylmethyl)amino]pyrimidin-4-yl}carbonyl)amino]benzyl}amino)butanoate

Product 1

HCID 251829242-({4-[({6-[Cyclohexyl(cyclopropylmethyl)amino]pyrimidin-4-yl}carbonyl)amino]benzyl}amino)butanoic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 2-({4-[({6-[cyclohexyl(cyclopropylmethyl)amino]pyrimidin-4-yl}carbonyl)amino]benzyl}amino)butanoate (Example 74, 50 mg; 0.10 mmol) in a mixture of MeOH (2 ml) and THF (2 ml) was treated with an aqueous solution (5 N) of sodium hydroxide (300 μl; 1.5 mmol) and the reaction mixture was stirred at room temperature for 24 hours. The mixture was acidified with HCl 1N until pH 4. The precipitate was filtered and dried under vacuum to give the title compound as a white solid.

Workup

  1. filtrationThe precipitate was filtered
  2. customdried under vacuum

Sources & evidence

ORD record
ord-abd0cfd02f0b4ee78d9673387f480e12
Source dataset
uspto-grants-2013_03
Patent number
US08399448B2

Reaction notes

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