Water → HCID 66665141, compound

HRID 872353Notes

Reaction equation

HRID 872353 reaction equation
[NH2:1][C:2]1([C:6]2[CH:11]=[CH:10][C:9]([C:12]3[N:13]=[C:14]4[CH:19]=[C:18]([OH:20])[CH:17]=[CH:16][N:15]4[C:21]=3[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:8][CH:7]=2)[CH2:5][CH2:4][CH2:3]1.Br[CH2:29][C:30]([O:32][CH3:33])=[O:31].C([O-])([O-])=O.[Cs+].[Cs+].O>CN(C=O)C>[CH3:33][O:32][C:30](=[O:31])[CH2:29][O:20][C:18]1[CH:17]=[CH:16][N:15]2[C:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[C:12]([C:9]3[CH:8]=[CH:7][C:6]([C:2]4([NH2:1])[CH2:3][CH2:4][CH2:5]4)=[CH:11][CH:10]=3)[N:13]=[C:14]2[CH:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 60984Methyl bromoacetateHCID 178507130HCID 178507130, compound

Product 1

HCID 66665141HCID 66665141, compoundYield 34.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-[4-(1-amino-cyclobutyl)-phenyl]-3-phenyl-imidazo[1,2-a]pyridin-7-ol (75 mg, 0.21 mmol), methyl bromoacetate (0.02 mL, 0.21 mmol, 1.0 equiv) and Cs2CO3 (138 mg, 0.422 mmol, 2 equiv) in DMF (2.5 mL) was stirred at room temperature for 12 h. The resulting mixture added to water (10 mL). The resulting mixture was extracted with EtOAc (3×10 mL). The combined organic phases were dried (Na2SO4 anh), and concentrated under reduced pressure. The remaining material was purified using MPLC (Biotage Isolera Flash NH2 Snap 10 reverse phase column; 100% CH2Cl2 for 8 min., gradient to 95% CH2Cl2: 5% MeOH over 5 min.; 95% CH2Cl2: 5% MeOH for 4 min., gradient to 80% CH2Cl2: 20% MeOH over 5 min., 80% CH2Cl2: 20% MeOH for 6.2 min., gradient to 75% CH2Cl2: 25% MeOH over 2.0 min., 75% CH2Cl2: 25% MeOH for 18.2 min.) to give {2-[4-(1-amino-cyclobutyl)-phenyl]-3-phenyl-imidazo[1,2-a]pyridin-7-yloxy}-acetic acid methyl ester (31 mg, 34%):

Workup

  1. extractionThe resulting mixture was extracted with EtOAc (3×10 mL)
  2. dry with materialThe combined organic phases were dried (Na2SO4 anh)
  3. concentrationconcentrated under reduced pressure
  4. customThe remaining material was purified
  5. waitgradient to 95% CH2Cl2: 5% MeOH over 5 min.
  6. wait95% CH2Cl2: 5% MeOH for 4 min.
  7. waitgradient to 80% CH2Cl2: 20% MeOH over 5 min.
  8. wait80% CH2Cl2: 20% MeOH for 6.2 min.
  9. waitgradient to 75% CH2Cl2: 25% MeOH over 2.0 min.

Sources & evidence

ORD record
ord-c55336e77f1a45f69566dfeeb71e50a8
Source dataset
uspto-grants-2015_03
Patent number
US08975265B2

Reaction notes

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