Diisopropylethylamine → HCID 86672807, compound

HRID 1755136Notes

Reaction equation

HRID 1755136 reaction equation
[CH2:1]([O:5][C:6]1[CH:7]=[C:8]([C:16]2[NH:20][C:19](=[O:21])[C:18]3([CH2:26][CH2:25][N:24]([S:27]([CH2:30][CH2:31][C:32]4[CH:40]=[CH:39][C:35]([C:36]([OH:38])=O)=[CH:34][C:33]=4[CH3:41])(=[O:29])=[O:28])[CH2:23][CH2:22]3)[N:17]=2)[CH:9]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:11]=1)[CH2:2][C:3]#[CH:4].Cl.[N:43]([CH2:46][CH2:47][CH2:48][NH:49][CH3:50])=[N+:44]=[N-:45].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.C(OCC)(=O)C>[N:43]([CH2:46][CH2:47][CH2:48][N:49]([CH3:50])[C:36](=[O:38])[C:35]1[CH:39]=[CH:40][C:32]([CH2:31][CH2:30][S:27]([N:24]2[CH2:23][CH2:22][C:18]3([N:17]=[C:16]([C:8]4[CH:9]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:11]=[C:6]([O:5][CH2:1][CH2:2][C:3]#[CH:4])[CH:7]=4)[NH:20][C:19]3=[O:21])[CH2:26][CH2:25]2)(=[O:28])=[O:29])=[C:33]([CH3:41])[CH:34]=1)=[N+:44]=[N-:45]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86672806HCID 86672806, compoundHCID 866728081254119-62-4

Product 1

HCID 86672807HCID 86672807, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-{2-[2-(3-But-3-ynyloxy-5-trifluoromethyl-phenyl)-4-oxo-1,3,8-triaza-spiro[4.5]dec-1-ene-8-sulfonyl]-ethyl}-3-methyl-benzoic acid, (3-azido-propyl)-methyl-amine hydrochloride (15.3 mg, 0.101 mmol) and DIPEA (0.044 ml, 0.255 mmol) were dissolved in DMF (0.400 ml). HATU (0.038 mg, 0.101 mmol) was added and the mixture was stirred at room temperature for one hour. The reaction solution was diluted with ethyl acetate, and the organic layer was then washed with a 1 M aqueous hydrochloric acid solution, an aqueous sodium bicarbonate solution and saline. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The resulting residue was purified by column chromatography (dichloromethane-ethyl acetate) to give N-(3-azido-propyl)-4-{2-[2-(3-but-3-ynyloxy-5-trifluoromethyl-phenyl)-4-oxo-1,3,8-triaza-spiro[4.5]dec-1-ene-8-sulfonyl]-ethyl}-3,N-dimethyl-benzamide as a colorless oily substance.

Workup

  1. washthe organic layer was then washed with a 1 M aqueous hydrochloric acid solution
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified by column chromatography (dichloromethane-ethyl acetate)

Sources & evidence

ORD record
ord-c9ba09b9f9c94233ab79eb64e67de4ec
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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