N,N-Dimethylglycine → HCID 10324121, compound

HRID 1768468Notes

Reaction equation

HRID 1768468 reaction equation
[Si]([O:8][CH2:9][C:10]1([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:14]=[C:13]([C:15]2[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:16]=2[F:22])[CH2:12][N:11]1[C:23]([N:25]([CH3:32])[CH:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1)=[O:24])(C(C)(C)C)(C)C.[CH3:39][N:40]([CH3:45])[CH2:41][C:42](O)=[O:43].CCN=C=NCCCN(C)C>C(Cl)Cl>[F:22][C:16]1[CH:17]=[CH:18][C:19]([F:21])=[CH:20][C:15]=1[C:13]1[CH2:12][N:11]([C:23]([N:25]([CH:26]2[CH2:27][CH2:28][N:29]([C:42](=[O:43])[CH2:41][N:40]([CH3:45])[CH3:39])[CH2:30][CH2:31]2)[CH3:32])=[O:24])[C:10]([CH2:9][OH:8])([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:14]=1

Participants

5

Reactant 3

HCID 673N,N-DimethylglycineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 10098834HCID 10098834, compound

Product 1

HCID 10324121HCID 10324121, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 30 mg (0.055 mmol) of amine 7-2 in CH2Cl2 was added 10 mg (0.097 mmol) of N,N-dimethylglycine and 15 mg (0.078 mmol) of EDCI. After stirring overnight at room temperature, the mixture was partitioned between CH2Cl2 and saturated NaHCO3, the layers were separated, the organic phase was washed with water, dried over Na2SO4, and concentrated by rotary evaporation. The residue was dissolved in dry CH3CN and ˜500 μL of 3HF-TEA was added and the mixture was stirred overnight at room temperature. The reaction was partitioned between EtOAc and saturated NaHCO3, the layers were separated, the organic phase was washed with brine, dried over Na2SO4, and concentrated by rotary evaporation. The residue was purified by reverse phase HPLC to provide 7-3 as a white solid. Data for 7-3: HRMS (ES) calc'd M+H for C28H34F2N4O3: 513.2672. Found: 513.2673.

Workup

  1. customthe mixture was partitioned between CH2Cl2 and saturated NaHCO3
  2. customthe layers were separated
  3. washthe organic phase was washed with water
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated by rotary evaporation
  6. dissolutionThe residue was dissolved in dry CH3CN
  7. addition˜500 μL of 3HF-TEA was added
  8. stirringthe mixture was stirred overnight at room temperature
  9. customThe reaction was partitioned between EtOAc and saturated NaHCO3
  10. customthe layers were separated
  11. washthe organic phase was washed with brine
  12. dry with materialdried over Na2SO4
  13. concentrationconcentrated by rotary evaporation
  14. customThe residue was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-898c4d0b70e24b7498ee19fb105bb325
Source dataset
uspto-grants-2007_06
Patent number
US07235580B2

Reaction notes

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