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

HRID 2200884Notes

Reaction equation

HRID 2200884 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

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 8028TetrahydrofuranSolvent

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]hexane hydrochloride salt (79 mg, 0.66 mmol). The solution was cooled in an ice bath, and triethylamine (167 mg, 1.65 mmol) was added dropwisely. The reaction was allowed to warm to ambient temperature for 5 h, followed by addition of water and extracted with DCM. The organic phase was dried and concentrated to give a solid which was used in the subsequent procedure without further purification.

Workup

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

Sources & evidence

ORD record
ord-ec6d8a4ba0e94617b6fa3d41830c869b
Source dataset
uspto-grants-2016_06
Patent number
US09359371B2

Reaction notes

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