1-Hydroxybenzotriazole → HCID 66960276, compound

HRID 2247607Notes

Reaction equation

HRID 2247607 reaction equation
C(N(C(C)C)CC)(C)C.C1C=CC2N(O)N=NC=2C=1.FC(F)(F)C(O)=O.[Cl:27][CH2:28][CH2:29][CH2:30]/[C:31](=[CH:35]\[C:36]1[CH:41]=[CH:40][C:39]([N:42]2[CH:46]=[C:45]([CH3:47])[N:44]=[CH:43]2)=[C:38]([O:48][CH3:49])[CH:37]=1)/[C:32]([OH:34])=O.[F:50][C:51]1[CH:59]=[C:58]2[C:54]([CH2:55][CH2:56][CH:57]2[NH2:60])=[CH:53][C:52]=1[N:61]1[CH2:66][CH2:65][O:64][CH2:63][CH2:62]1>CN(C=O)C.C(Cl)CCl>[F:50][C:51]1[CH:59]=[C:58]2[C:54]([CH2:55][CH2:56][CH:57]2[NH:60][C:32](=[O:34])/[C:31](=[CH:35]/[C:36]2[CH:41]=[CH:40][C:39]([N:42]3[CH:46]=[C:45]([CH3:47])[N:44]=[CH:43]3)=[C:38]([O:48][CH3:49])[CH:37]=2)/[CH2:30][CH2:29][CH2:28][Cl:27])=[CH:53][C:52]=1[N:61]1[CH2:66][CH2:65][O:64][CH2:63][CH2:62]1

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 66960186(E)-5-chloro-2-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene)valeric acid trifluoroacetateHCID 66961806HCID 66961806, compound

Product 1

HCID 66960276HCID 66960276, compoundYield 93.8%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6228DimethylformamideSolvent

Procedure

IPEA (165 μL), EDC (90.9 mg) and HOBT (64.0 mg) were sequentially added to a solution of (E)-5-chloro-2-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene)valeric acid trifluoroacetate (138 mg) and 6-fluoro-5-morpholin-4-ylindan-1-ylamine (56.0 mg) in DMF (3.0 mL), and the reaction solution was stirred at room temperature for 1 hour. After confirming that the raw materials disappeared, the solvent was concentrated under reduced pressure, and water and ethyl acetate were added to the residue and the organic layer was partitioned. The organic layer was washed with brine, and then dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (elution solvent: heptane-ethyl acetate system, ethyl acetate-methanol system) to obtain 123 mg of the title compound. The physical properties of the compound are as follows.

Workup

  1. concentrationthe solvent was concentrated under reduced pressure, and water and ethyl acetate
  2. additionwere added to the residue
  3. customthe organic layer was partitioned
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by silica gel chromatography (elution solvent: heptane-ethyl acetate system, ethyl acetate-methanol system)

Sources & evidence

ORD record
ord-c33d552fa9b5498bb45d82a7296e3eb8
Source dataset
uspto-grants-2010_03
Patent number
US07687640B2

Reaction notes

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