Diisopropylamine → HCID 58823994, compound

HRID 1893748Notes

Reaction equation

HRID 1893748 reaction equation
[C:1]([O:5][C:6](=[O:44])[CH2:7][CH:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([C:18](O)=O)[CH:16]=2)[N:11]=[C:10]([N:21]2[CH2:26][CH2:25][N:24]([C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=3)[CH2:23][CH2:22]2)[N:9]1[C:34]1[CH:39]=[CH:38][CH:37]=[C:36]([C:40]([F:43])([F:42])[F:41])[CH:35]=1)([CH3:4])([CH3:3])[CH3:2].[Cl-].[Al+3].[Cl-].[Cl-].[OH2:49].O[N:51]1C2C=CC=CC=2N=N1.CN(C)CCCN=C=NCC.C(NC(C)C)(C)C>CN(C=O)C.C(OCC)(=O)C>[NH2:51][C:18]([C:15]1[CH:16]=[C:17]2[C:12](=[CH:13][CH:14]=1)[N:11]=[C:10]([N:21]1[CH2:22][CH2:23][N:24]([C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=3)[CH2:25][CH2:26]1)[N:9]([C:34]1[CH:39]=[CH:38][CH:37]=[C:36]([C:40]([F:41])([F:43])[F:42])[CH:35]=1)[CH:8]2[CH2:7][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:44])=[O:49]

Participants

8

Reactant 5

HCID 7912DiisopropylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 27960291-Hydroxybenzotriazole hydrateHCID 6451240Aluminum(III) ChlorideHCID 18444400HCID 18444400, compound

Product 1

HCID 58823994HCID 58823994, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

560 mg (0.9 mmol) of the carboxylic acid from Example 48A, 2.6 mmol of aluminium chloride, 1.1 mmol of 1-hydroxy-1H-benzotriazole hydrate and 1.1 mmol of N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide are suspended in DMF. 2.6 mmol of N,N-diisopropylamine are added, and the mixture is stirred at room temperature for 16 hours. 20 ml of ethyl acetate are added to the reaction mixture, which is then washed with a saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium chloride solution. The combined aqueous phases are adjusted to pH=8 and extracted with ethyl acetate. The combined organic phases are finally washed with a saturated aqueous sodium chloride solution, dried over sodium sulphate and concentrated. This gives 548 mg (97% of theory) of product.

Workup

  1. washis then washed with a saturated aqueous sodium bicarbonate solution
  2. extractionextracted with ethyl acetate
  3. washThe combined organic phases are finally washed with a saturated aqueous sodium chloride solution
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-f84575170b374eecada2b9345353d07a
Source dataset
uspto-grants-2013_08
Patent number
US08513255B2

Reaction notes

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