HOAt → HCID 57581474, compound

HRID 1689973Notes

Reaction equation

HRID 1689973 reaction equation
[CH3:1][C@@H:2]1[CH2:7][NH:6][CH2:5][CH2:4][N:3]1[C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[N:10][N:9]=1.[O:24]=[C:25]1[CH2:30][CH2:29][CH:28]([C:31](O)=[O:32])[CH2:27][CH2:26]1.N1C2C(=NC=CC=2)N(O)N=1.Cl.C(N=C=NCCCN(C)C)C.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C.CN(C=O)C>[CH3:1][C@@H:2]1[CH2:7][N:6]([C:31]([CH:28]2[CH2:29][CH2:30][C:25](=[O:24])[CH2:26][CH2:27]2)=[O:32])[CH2:5][CH2:4][N:3]1[C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[N:10][N:9]=1

Participants

8

Reactant 5

HCID 181649HOAtHCID 1927304-Oxocyclohexanecarboxylic acidHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57581524HCID 57581524, compound

Product 1

HCID 57581474HCID 57581474, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

(R)-1-(2-methylpiperazin-1-yl)-4-phenylphthalazine (JK-10) (509 mg, 1.67 mmol), 4-oxocyclohexanecarboxylic acid (261 mg, 1.84 mmol), 3H-[1,2,3]triazolo[4,5-b]pyridin-3-ol (273 mg, 2.01 mmol) (HOAt), N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (385 mg, 2.01 mmol), sodium bicarbonate (281 mg, 3.34 mmol), and DMF (6 mL) were stirred at rt for 22 hours. The reaction was taken up in ethyl acetate (80 mL) and washed with aqueous K2CO3 (10%), water, and saturated sodium chloride. The organics were dried (MgSO4) and evaporated to give a yellow oil. Chromatography over silica gel with a gradient of hexanes/0-70% ethyl acetate gave an off-white solid, compound 69. MS (M+H)+=429.2.

Workup

  1. washwashed with aqueous K2CO3 (10%), water, and saturated sodium chloride
  2. dry with materialThe organics were dried (MgSO4)
  3. customevaporated
  4. customto give a yellow oil

Sources & evidence

ORD record
ord-ecb18d3f8d77472aa9a39c8218656c99
Source dataset
uspto-grants-2012_04
Patent number
US08153633B2

Reaction notes

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