Water → HCID 11583783, compound

HRID 499916Notes

Reaction equation

HRID 499916 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][N:5]1[CH:9]=[C:8]([NH:10][C:11]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][C:21]([F:24])([F:23])[F:22])=[CH:16][CH:15]=2)=[O:12])[N:7]=[C:6]1[C:25]([OH:27])=O.C1N=CN(C(N2C=NC=C2)=O)C=1.O.[N:41]1[CH:46]=[CH:45][CH:44]=[C:43]([CH2:47][NH2:48])[CH:42]=1>CN(C=O)C>[CH3:1][O:2][CH2:3][CH2:4][N:5]1[CH:9]=[C:8]([NH:10][C:11]([NH:13][C:14]2[CH:15]=[CH:16][C:17]([O:20][C:21]([F:23])([F:22])[F:24])=[CH:18][CH:19]=2)=[O:12])[N:7]=[C:6]1[C:25]([NH:48][CH2:47][C:43]1[CH:42]=[N:41][CH:46]=[CH:45][CH:44]=1)=[O:27]

Participants

6

Reactant 4

HCID 962WaterHCID 310183-PyridinemethanamineHCID 682631,1'-CarbonyldiimidazoleHCID 59421782HCID 59421782, compound

Product 1

HCID 11583783HCID 11583783, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

38.8 mg (0.1 mmol) of 1-(2-methoxyethyl)-4-[({[4-(trifluoromethoxy)phenyl]amino}-carbonyl)amino]-1H-imidazole-2-carboxylic acid (Example 9A) are dissolved in 0.4 ml of DMF and, after addition of 81 mg (0.5 mmol) of N,N-carbonyldiimidazole, stirred at room temperature for 50 minutes. Then 18 μl (18 mg; 1 mmol) of water are added, and the mixture is stirred at room temperature for 30 minutes. Addition of 21.6 mg (0.2 mmol) of 3-picolylamine is followed by stirring at room temperature for 90 minutes. After filtration, the reaction mixture is purified by preparative HPLC (column: Macherey-Nagel VP 50/21 Nucleodur C18 gravity, 5 μm; flow rate: 25 ml/min; eluent A: acetonitrile, eluent B: water+0.1% conc. aqueous ammonia solution, gradient: 0 min 10% A, 2.00 min 10% A, 6.00 min 90% A, 7.00 min 90% A, 7.10 min 10% A, 8 min 10% A; running time: ca. 10 min per separation; wave length: 220 nm). The correct fractions are evaporated in vacuo.

Workup

  1. stirringthe mixture is stirred at room temperature for 30 minutes
  2. stirringby stirring at room temperature for 90 minutes
  3. filtrationAfter filtration
  4. customthe reaction mixture is purified by preparative HPLC (column: Macherey-Nagel VP 50/21 Nucleodur C18 gravity, 5 μm; flow rate: 25 ml/min; eluent A: acetonitrile, eluent B: water+0.1% conc. aqueous ammonia solution, gradient: 0 min 10% A, 2.00 min 10% A, 6.00 min 90% A, 7.00 min 90% A, 7.10 min 10% A, 8 min 10% A; running time: ca. 10 min per separation; wave length: 220 nm)
  5. customThe correct fractions are evaporated in vacuo

Sources & evidence

ORD record
ord-aa29c7a2e64a4090af888d6a2c14fb05
Source dataset
uspto-grants-2010_08
Patent number
US07767704B2

Reaction notes

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