Sodium Hydroxide → 1-{6-[5-Oxo-4-(1H-1,2,3-triazol-1-yl)-2,5-dihydro-1H-pyrazol-1-yl]pyrimidin-4-yl}azetidine-3-carboxylic acid

HRID 2039488Notes

Reaction equation

HRID 2039488 reaction equation
Cl.[NH:2]1[CH2:5][CH:4]([C:6]([OH:8])=[O:7])[CH2:3]1.Cl.Cl[C:11]1[N:16]=[CH:15][N:14]=[C:13]([N:17]2[C:21](=[O:22])[C:20]([N:23]3[CH:27]=[CH:26][N:25]=[N:24]3)=[CH:19][NH:18]2)[CH:12]=1.[OH-].[Na+]>O>[O:22]=[C:21]1[N:17]([C:13]2[N:14]=[CH:15][N:16]=[C:11]([N:2]3[CH2:5][CH:4]([C:6]([OH:8])=[O:7])[CH2:3]3)[CH:12]=2)[NH:18][CH:19]=[C:20]1[N:23]1[CH:27]=[CH:26][N:25]=[N:24]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 13374356Azetidine-3-carboxylic acid--hydrogen chloride (1/1)HCID 866352542-(6-Chloropyrimidin-4-yl)-4-(1H-1,2,3-triazol-1-yl)-1,2-dihydro-3H-pyrazol-3-one hydrochloride

Product 1

HCID 444646101-{6-[5-Oxo-4-(1H-1,2,3-triazol-1-yl)-2,5-dihydro-1H-pyrazol-1-yl]pyrimidin-4-yl}azetidine-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

55 mg (0.4 mmol) of azetidine-3-carboxylic acid hydrochloride are initially charged in 2 ml of water. 100 mg (0.3 mmol) of the compound from Example 12A are added, and the pH is adjusted to 7 using aqueous 1 N sodium hydroxide solution. The mixture is reacted in a single mode microwave (Emrys Optimizer) at 150° C. for 1 h. The reaction mixture is concentrated under reduced pressure and purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient). Yield: 15 mg (13% of theory)

Workup

  1. customThe mixture is reacted in a single mode microwave (Emrys Optimizer) at 150° C. for 1 h
  2. concentrationThe reaction mixture is concentrated under reduced pressure
  3. custompurified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient)

Sources & evidence

ORD record
ord-e0994f09d06948328b8dc21da6505ad4
Source dataset
uspto-grants-2013_11
Patent number
US08580778B2

Reaction notes

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