Dimethylformamide → HCID 10204670, compound

HRID 1591698Notes

Reaction equation

HRID 1591698 reaction equation
COC(=O)[CH2:4][NH:5][S:6]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH:17]2[CH2:19][CH2:18]2)=[CH:11][CH:10]=1)(=[O:8])=[O:7].Cl[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([N:29]2[N:33]=[CH:32][CH:31]=[N:30]2)=[CH:25][CH:24]=1.C([O-])([O-])=[O:35].[K+].[K+].C[N:41]([CH:43]=[O:44])C>>[CH:17]1([CH2:16][O:15][C:12]2[CH:11]=[CH:10][C:9]([S:6]([N:5]([CH2:4][C:43]([NH:41][OH:35])=[O:44])[CH2:22][C:23]3[CH:28]=[CH:27][C:26]([N:29]4[N:33]=[CH:32][CH:31]=[N:30]4)=[CH:25][CH:24]=3)(=[O:7])=[O:8])=[CH:14][CH:13]=2)[CH2:18][CH2:19]1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 219436922H-1,2,3-Triazole, 2-[4-(chloromethyl)phenyl]-HCID 68686408HCID 68686408, compound

Product 1

HCID 10204670HCID 10204670, compound

Procedure

To a solution of 1 g (3.3 mmol) of the compound of Stage 3.7 in 10 ml of DMF, 0.8086 g (4.175 mmol) of 2-(4-chloromethyl-phenyl)-2H-[1,2,3]triazole, 0.0555 g (0.33 mmol) of KI and 0.646 g (4.68 mmol) of K2CO3 are added successively at r.t. After stirring for 18 h, the reaction is quenched with ice water and the mixture is extracted with AcOEt. The combined extracts are washed with H2O, brine, dried over MgSO4 and concentrated under reduced pressure to give a solid which is washed with diethylether and MeOH to give the title compound.

Workup

  1. customthe reaction is quenched with ice water
  2. extractionthe mixture is extracted with AcOEt
  3. washThe combined extracts are washed with H2O, brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customto give a solid which
  7. washis washed with diethylether and MeOH

Sources & evidence

ORD record
ord-fe32f782ce0f47c19999370b0084503f
Source dataset
uspto-grants-2007_11
Patent number
US07291634B2

Reaction notes

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