1-Hydroxybenzotriazole → HCID 86700056, compound

HRID 1428105Notes

Reaction equation

HRID 1428105 reaction equation
CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.[CH3:23][C:24]1([CH3:38])[C:28]([CH3:30])([CH3:29])[O:27][B:26]([C:31]2[CH:37]=[CH:36][C:34]([NH2:35])=[CH:33][CH:32]=2)[O:25]1.[CH2:39]([N:46]1[CH:51]=[C:50]([C:52]2[CH:57]=[CH:56][C:55]([F:58])=[CH:54][CH:53]=2)[C:49](=[O:59])[C:48]([C:60](O)=[O:61])=[CH:47]1)[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>CN(C=O)C.O>[CH2:39]([N:46]1[CH:51]=[C:50]([C:52]2[CH:53]=[CH:54][C:55]([F:58])=[CH:56][CH:57]=2)[C:49](=[O:59])[C:48]([C:60]([NH:35][C:34]2[CH:36]=[CH:37][C:31]([B:26]3[O:25][C:24]([CH3:38])([CH3:23])[C:28]([CH3:29])([CH3:30])[O:27]3)=[CH:32][CH:33]=2)=[O:61])=[CH:47]1)[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride2×HCID 27346204-(Tetramethyl-1,3,2-dioxaborolan-2-yl)aniline2×HCID 86700036HCID 86700036, compound

Product 1

HCID 86700056HCID 86700056, compoundYield 40.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

EDC.HCl (152 mg), HOBt (73 mg) and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (128 mg) were added to a solution of 1-benzyl-5-(4-fluorophenyl)-4-oxo-1,4-dihydropyridine-3-carboxylic acid (171 mg) in DMF (3 ml) at room temperature. The reaction mixture was stirred at 50° C. overnight. EDC.HCl (76 mg) and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (64 mg) were added to the reaction mixture at 50° C. The reaction mixture was stirred at 50° C. overnight. The reaction mixture was stirred at 80° C. overnight. The reaction mixture was returned to room temperature and diluted by adding water. The precipitated solid was collected by filtration. The resulting solid was purified by silica gel column chromatography [hexane:ethyl acetate=5:1->4:1->3:1->1:1 (v/v)] to give 112 mg of the title compound as a solid.

Workup

  1. stirringThe reaction mixture was stirred at 50° C. overnight
  2. stirringThe reaction mixture was stirred at 80° C. overnight
  3. customwas returned to room temperature
  4. additiondiluted
  5. filtrationThe precipitated solid was collected by filtration
  6. customThe resulting solid was purified by silica gel column chromatography [hexane:ethyl acetate=5:1->4:1->3:1->1:1 (v/v)]

Sources & evidence

ORD record
ord-7e5abd2e0aac462588a0ccfea95727f2
Source dataset
uspto-grants-2015_01
Patent number
US08933103B2

Reaction notes

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