Hydrochloric Acid → 2-(6-{[(Naphthalen-2-ylmethyl)amino]methyl}-3-azabicyclo[3.1.0]hex-3-yl)pyrimidine-5-carboxylic acid

HRID 2079812Notes

Reaction equation

HRID 2079812 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][NH:12][CH2:13][CH:14]1[CH:19]2[CH:15]1[CH2:16][N:17]([C:20]1[N:25]=[CH:24][C:23]([C:26]([O:28]CC)=[O:27])=[CH:22][N:21]=1)[CH2:18]2.[OH-].[Na+].Cl>C1COCC1>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][NH:12][CH2:13][CH:14]1[CH:15]2[CH:19]1[CH2:18][N:17]([C:20]1[N:25]=[CH:24][C:23]([C:26]([OH:28])=[O:27])=[CH:22][N:21]=1)[CH2:16]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 49855398HCID 49855398, compound

Product 1

HCID 498575172-(6-{[(Naphthalen-2-ylmethyl)amino]methyl}-3-azabicyclo[3.1.0]hex-3-yl)pyrimidine-5-carboxylic acidYield 25.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 2-(6-{[(naphthalen-2-ylmethyl)amino]methyl}-3-aza-bicyclo[3.1.0]hex-3-yl)-pyrimidine-5-carboxylate (0.76 mmol) was stirred in THF (6 ml) and 1M NaOH (6 ml) at r.t. for 16 h. The reaction was then acidified to pH˜3 with 2M HCl, causing a solid to precipitate. This was collected and dried to give the title compound as a white solid (72 mg, 25% over two steps) which was used in the next step without further purification. LCMS purity 96%, m/z 375 [M+H]+.

Workup

  1. customto precipitate
  2. customThis was collected
  3. customdried

Sources & evidence

ORD record
ord-16c3cca50b694a299a57e6e14d8890db
Source dataset
uspto-grants-2011_04
Patent number
US07932246B2

Reaction notes

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