Diisopropylethylamine → azanium (2E)-2-[[4-(3,4-dichlorophenyl)-1,3-thiazol-2-yl]hydrazinylidene]-3-(4-pyridin-2-yltriazol-1-yl)propanoate

HRID 871067Notes

Reaction equation

HRID 871067 reaction equation
[N:1]([CH2:4]/[C:5](=[N:9]\[NH:10][C:11]1[S:12][CH:13]=[C:14]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([Cl:23])[CH:17]=2)[N:15]=1)/[C:6]([OH:8])=[O:7])=[N+:2]=[N-:3].C([N:27](C(C)C)CC)(C)C.[C:33]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][N:36]=1)#[CH:34]>CC#N.C(O)(C)(C)C.[Cu]I>[Cl:23][C:18]1[CH:17]=[C:16]([C:14]2[N:15]=[C:11]([NH:10]/[N:9]=[C:5](\[CH2:4][N:1]3[CH:34]=[C:33]([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][N:36]=4)[N:3]=[N:2]3)/[C:6]([O-:8])=[O:7])[S:12][CH:13]=2)[CH:21]=[CH:20][C:19]=1[Cl:22].[NH4+:27]

Participants

7

Reactant 3

HCID 81531DiisopropylethylamineHCID 137268EthynylpyridineHCID 89676234(2E)-3-azido-2-[[4-(3,4-dichlorophenyl)-1,3-thiazol-2-yl]hydrazinylidene]propanoic acid

Product 1

HCID 140611604azanium (2E)-2-[[4-(3,4-dichlorophenyl)-1,3-thiazol-2-yl]hydrazinylidene]-3-(4-pyridin-2-yltriazol-1-yl)propanoate

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6342AcetonitrileSolventHCID 6386tert-ButanolSolvent

Procedure

KY-767-batch-A To a solution of (E)-3-azido-2-(2-(4-(3,4-dichlorophenyl)thiazol-2-yl)hydrazono) propanoic acid (E)-KY-757, (100 mg) in CH3CN 1 ml, tert-butanol 0.4 ml was added diisopropylethylamine 96 ul followed by 2-ethynylpyridine (0.4 mmol, 41 ul), CuI (15 mg). The reaction stirred at rt for 3 h. LC-MS assay showed two isomers. The solvent was removed under pressure. The residue was purified on C18 reversed phase flash chromatography column employing a linear gradient of 0-30% A in B (flow rate 40 ml/min), were A is 10% NH4OH in CH3CN and B is water, yielding (14 mg, 18%) of pure (E)-KY-788. MS+(ESI) m/z 373.91, calcd mass 473.85.

Workup

  1. customThe solvent was removed under pressure
  2. customThe residue was purified on C18 reversed phase flash chromatography column
  3. customyielding (14 mg, 18%) of pure (E)-KY-788

Sources & evidence

ORD record
ord-90458f3d685c4de9a906d43a869ecd24
Source dataset
uspto-grants-2015_03
Patent number
US08969573B2

Reaction notes

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