2-Dimethylaminopyridine → HCID 53327513, compound

HRID 1465999Notes

Reaction equation

HRID 1465999 reaction equation
[C:1](=[O:19])(OC1C=CC([N+]([O-])=O)=CC=1)[O:2][CH2:3][C:4]1[N:5]=[CH:6][S:7][CH:8]=1.[F:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[CH:32]=[CH:31][C:30]([O:33][CH2:34][CH:35]3[CH2:39][CH2:38][NH:37][CH2:36]3)=[CH:29][CH:28]=2)=[CH:23][CH:22]=1.C(N(CC)C(C)C)(C)C.CN(C1C=CC=CN=1)C>ClCCCl.O>[F:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[CH:32]=[CH:31][C:30]([O:33][CH2:34][CH:35]3[CH2:39][CH2:38][N:37]([C:1]([O:2][CH2:3][C:4]4[N:5]=[CH:6][S:7][CH:8]=4)=[O:19])[CH2:36]3)=[CH:29][CH:28]=2)=[CH:23][CH:22]=1

Participants

7

Reactant 4

HCID 218852-DimethylaminopyridineHCID 81531DiisopropylethylamineHCID 18939632HCID 18939632, compoundHCID 67326759HCID 67326759, compound

Product 1

HCID 53327513HCID 53327513, compoundYield 36.3%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

0.30 g (1.07 mmol) of thiazol-4-ylmethyl 4-nitrophenyl carbonate, 0.34 g (1.28 mmol) of 3-(4′-fluorobiphenyl-4-yloxymethyl)pyrrolidine, 0.20 g (1.61 mmol) of N,N-diisopropylethylamine and 0.01 g (0.11 mmol) of dimethylaminopyridine are dissolved in 10 ml of 1,2-dichloroethane. The mixture is stirred at 70° C. for 4 hours. After returning to ambient temperature, water is added to the reaction medium. After extraction of the aqueous phase with dichloromethane, the organic phases are successively washed three times with a 1M aqueous sodium hydroxide solution and then twice with a saturated aqueous ammonium chloride solution. After having dried the organic phases over sodium sulphate, they are filtered and the filtrate is evaporated to dryness. After purification by chromatography on a column of silica gel, elution being carried out with dichloromethane and methanol (98/2), 0.16 g of the expected product is obtained in the form of a powder.

Workup

  1. customAfter returning to ambient temperature
  2. extractionAfter extraction of the aqueous phase with dichloromethane
  3. washthe organic phases are successively washed three times with a 1M aqueous sodium hydroxide solution
  4. dry with materialAfter having dried the organic phases over sodium sulphate, they
  5. filtrationare filtered
  6. customthe filtrate is evaporated to dryness
  7. customAfter purification by chromatography
  8. washon a column of silica gel, elution

Sources & evidence

ORD record
ord-716451d76a894b11b7f19be9af9b69d9
Source dataset
uspto-grants-2015_04
Patent number
US09000010B2

Reaction notes

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