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Water → 2-(3-Azabicyclo[3.1.0]hexan-3-yl)-4-((3-chloro-4-methoxybenzyl)amino)pyrimidine-5-carboxylic acid

HRID 2200868
Notes
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Reaction equation

HRID 2200868 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][C:21]=1[O:22][CH3:23])[CH2:5][NH:6][C:7]1[C:12]([C:13]([OH:15])=[O:14])=[CH:11][N:10]=[C:9](S(C)=O)[N:8]=1.Cl.[CH:25]12[CH2:30][CH:29]1[CH2:28][NH:27][CH2:26]2.C(N(CC)CC)C.O>C1COCC1>[CH:25]12[CH2:30][CH:29]1[CH2:28][N:27]([C:9]1[N:8]=[C:7]([NH:6][CH2:5][C:4]3[CH:19]=[CH:20][C:21]([O:22][CH3:23])=[C:2]([Cl:1])[CH:3]=3)[C:12]([C:13]([OH:15])=[O:14])=[CH:11][N:10]=1)[CH2:26]2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 223352893-Azabicyclo[3.1.0]hexane hydrochlorideHCID 118157672Avanafil Impurity 37

Product 1

HCID 1176225452-(3-Azabicyclo[3.1.0]hexan-3-yl)-4-((3-chloro-4-methoxybenzyl)amino)pyrimidine-5-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

In THF (15 mL) were dissolved 4-((3-chloro-4-methoxybenzyl)amino)-2-(methylsulfinyl)pyrimidine-5-carboxylic acid (196 mg, 0.55 mmol) and 3-azabicyclo[3.1.0]hexan hydrochloride salt (79 mg, 0.66 mmol). The solution was cooled in an ice bath and triethylamine (167 mg, 1.65 mmol) was then added dropwisely. The reaction was warmed to ambient temperature for 5 h. Then water was added and the reaction mixture was extracted with DCM. The organic phase was dried and concentrated to give a solid. The product was used in the subsequent procedure without further purification.

Workup

  1. temperatureThe solution was cooled in an ice bath
  2. extractionthe reaction mixture was extracted with DCM
  3. customThe organic phase was dried
  4. concentrationconcentrated
  5. customto give a solid
  6. customThe product was used in the subsequent procedure without further purification

Sources & evidence

ORD record
ord-2a135e321bc746c083e1e3ff2ea8e92d
Source dataset
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09359371B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes