1-Hydroxybenzotriazole → HCID 66961708, compound

HRID 1446593Notes

Reaction equation

HRID 1446593 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.[N:50]1([C:56]2[CH:65]=[C:64]3[C:59]([CH2:60][CH2:61][CH2:62][CH:63]3[NH2:66])=[CH:58][CH:57]=2)[CH2:55][CH2:54][O:53][CH2:52][CH2:51]1>CN(C=O)C.C(OCC)(=O)C.O.C(Cl)CCl>[N:50]1([C:56]2[CH:65]=[C:64]3[C:59]([CH2:60][CH2:61][CH2:62][CH:63]3[NH:66][C:32](=[O:34])/[C:31](=[CH:35]/[C:36]3[CH:41]=[CH:40][C:39]([N:42]4[CH:46]=[C:45]([CH3:47])[N:44]=[CH:43]4)=[C:38]([O:48][CH3:49])[CH:37]=3)/[CH2:30][CH2:29][CH2:28][Cl:27])=[CH:58][CH:57]=2)[CH2:55][CH2:54][O:53][CH2:52][CH2:51]1

Participants

9

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 66960186(E)-5-chloro-2-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene)valeric acid trifluoroacetateHCID 66961235HCID 66961235, compound

Product 1

HCID 66961708HCID 66961708, compoundYield 81.9%

Reagents, catalysts & solvents 4

HCID 111,2-DichloroethaneSolventHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

IPEA (330 μL), EDC (181 mg) and HOBT (128 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 (276 mg) and 7-morpholin-4-yl-1,2,3,4-tetrahydronaphthalen-1-ylamine (110 mg) in DMF (3.0 mL) at room temperature, and the reaction solution was stirred at room temperature for 30 minutes. After confirming that the raw materials disappeared, 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 213 mg of the title compound. The physical properties of the compound are as follows.

Workup

  1. customthe organic layer was partitioned
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel chromatography (elution solvent:heptane-ethyl acetate system→ethyl acetate-methanol system)

Sources & evidence

ORD record
ord-6d3be256dd04462b94315ae4273e352e
Source dataset
uspto-grants-2010_02
Patent number
US07667041B2

Reaction notes

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