Triethylamine → HCID 69199810, compound

HRID 2252241Notes

Reaction equation

HRID 2252241 reaction equation
[I:1][C:2]1[C:3]2[CH2:13][C:12]3[C:7](=[CH:8][CH:9]=[C:10]([C:14]([NH:16][CH2:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=4)=[O:15])[CH:11]=3)[C:4]=2[NH:5][N:6]=1.[CH3:24][O:25][C:26]1[CH:31]=[CH:30][C:29]([CH:32](Cl)[C:33]2[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][CH:34]=2)=[CH:28][CH:27]=1.CCN(CC)CC>CN(C=O)C.[Cl-].[Na+].O>[CH3:40][O:39][C:36]1[CH:35]=[CH:34][C:33]([CH:32]([C:29]2[CH:30]=[CH:31][C:26]([O:25][CH3:24])=[CH:27][CH:28]=2)[N:5]2[C:4]3[C:7]4[C:12]([CH2:13][C:3]=3[C:2]([I:1])=[N:6]2)=[CH:11][C:10]([C:14]([NH:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)=[O:15])=[CH:9][CH:8]=4)=[CH:38][CH:37]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 10706646bis(4-methoxyphenyl)chloromethaneHCID 178522964HCID 178522964, compound

Product 1

HCID 69199810HCID 69199810, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A mixture of Example 124A (0.176 g, 0.423 mmol), bis-(4-methoxy-phenyl)-methyl chloride (0.122 g, 0.465 mmol), and Et3N (71 μL, 0.507 mmol) in DMF (2.0 mL) was stirred at room temperature for 4 hours. The reaction mixture was diluted with 50% brine and extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4, filtered, concentrated, and purified by flash chromatography eluted with EtOAc to give 0.166 g (61%) of the desired as pale yellow solid. MS (ESI) m/z: 643.1 (M+H)+.

Workup

  1. extractionextracted with EtOAc
  2. washThe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by flash chromatography
  7. washeluted with EtOAc
  8. customto give 0.166 g (61%) of the

Sources & evidence

ORD record
ord-51c9957dd1b0499aa7717fd034953209
Source dataset
uspto-grants-2008_01
Patent number
US07320986B2

Reaction notes

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