Dimethylamine → HCID 68698324, compound

HRID 1990882Notes

Reaction equation

HRID 1990882 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:27]=[CH:28][C:29]=1[O:30][CH3:31])[CH2:7][N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[O:16][C:17]3[C:23]([C:24]([OH:26])=O)=[CH:22][CH:21]=[CH:20][C:18]=3[N:19]=2)[CH2:10][CH2:9]1)[CH3:2].C1N=[CH:35][N:34](C(N2C=NC=C2)=O)[CH:33]=1.CNC.C(O)C>CN(C=O)C>[CH3:33][N:34]([CH3:35])[C:24]([C:23]1[C:17]2[O:16][C:15]([NH:14][CH:11]3[CH2:10][CH2:9][N:8]([CH2:7][C:6]4[CH:27]=[CH:28][C:29]([O:30][CH3:31])=[C:4]([O:3][CH2:1][CH3:2])[CH:5]=4)[CH2:13][CH2:12]3)=[N:19][C:18]=2[CH:20]=[CH:21][CH:22]=1)=[O:26]

Participants

6

Reactant 4

HCID 674DimethylamineHCID 702EthanolHCID 682631,1'-CarbonyldiimidazoleHCID 58706340HCID 58706340, compound

Product 1

HCID 68698324HCID 68698324, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To the crude coupling product 2-[1-(3-ethoxy-4-methoxy-benzyl)-piperidin-4-ylamino]-benzo-oxazole-7-carboxylic acid (42.5 mg, 0.1 mmol, 1.0 equiv) dissolved in anhydrous DMF (1 mL) was added CDI (32.4 mg, 0.2 mmol, 2.0 equiv) and the reaction mixture stirred at 50° C. After 1 h, a solution of dimethylamine 5.6 M in ethanol (71 μL, 0.4 mmol, 4.0 equiv) was added and the reaction mixture stirred at 50° C. for another 24 h. Removal of the solvent under reduced pressure and purification by preparative HPLC on reversed phase eluting with a gradient of acetonitrile/water provided 9.0 mg (20%) of the title compound. MS (ESI): 452.0 [M+H]+.

Workup

  1. stirringthe reaction mixture stirred at 50° C. for another 24 h
  2. customRemoval of the solvent
  3. customunder reduced pressure and purification by preparative HPLC on reversed phase
  4. washeluting with a gradient of acetonitrile/water

Sources & evidence

ORD record
ord-99d9149f6aaa450b973f1802560eb145
Source dataset
uspto-grants-2010_01
Patent number
US07645753B2

Reaction notes

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