Hydrochloric Acid → 5-(3,5-Dioxo-4,5-dihydro-3H-[1,2,4]triazin-2-yl)-N-(1-hydroxy-cycloheptylmethyl)-2-methyl-benzamide

HRID 347665

Reaction equation

HRID 347665 reaction equation
[O:1]=[C:2]1[NH:7][C:6](=[O:8])[CH:5]=[N:4][N:3]1[C:9]1[CH:10]=[CH:11][C:12]([CH3:18])=[C:13]([CH:17]=1)[C:14]([OH:16])=O.Cl.[NH2:20][CH2:21][C:22]1([OH:29])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1.CCN=C=NCCCN(C)C.Cl.Cl>CN(C1C=CN=CC=1)C.CN(C=O)C.O>[O:1]=[C:2]1[NH:7][C:6](=[O:8])[CH:5]=[N:4][N:3]1[C:9]1[CH:10]=[CH:11][C:12]([CH3:18])=[C:13]([CH:17]=1)[C:14]([NH:20][CH2:21][C:22]1([OH:29])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1)=[O:16]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 184386471-(Aminomethyl)cycloheptan-1-ol--hydrogen chloride (1/1)HCID 222674555-(3,5-Dioxo-4,5-dihydro-1,2,4-triazin-2(3H)-yl)-2-methylbenzoic acid

Product 1

HCID 545854355-(3,5-Dioxo-4,5-dihydro-3H-[1,2,4]triazin-2-yl)-N-(1-hydroxy-cycloheptylmethyl)-2-methyl-benzamideYield 41.2%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A slurry of 5-(3,5-Dioxo-4,5-dihydro-3H-[1,2,4]triazin-2-yl)-2-methyl-benzoic acid (5.0 g, 20.2 mmol), 1-aminomethyl-cycloheptanol HCl (5.4 g, 30.3 mmol), EDCl (5.8 g), and DMAP (7.4 g, 60.6 mmol) in DMF (67.3 mL) was stirred at ambient temperature for 14 hours. The reaction was then poured into 1N HCl (50 mL) and diluted with water (15 fold). The aqueous was extracted with CH2Cl2 (3×). The organics were combined, washed with brine, dried over sodium sulfate, and concentrated in vacuo to give a tan solid. The crude was recrystallized from CH2Cl2 to give the title compound as an off-white solid (3.1 g).

Workup

  1. extractionThe aqueous was extracted with CH2Cl2 (3×)
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customto give a tan solid
  6. customThe crude was recrystallized from CH2Cl2

Sources & evidence

ORD record
ord-fde5718c817e43e4adcc6bf7cf3f450c
Source dataset
uspto-grants-2007_02
Patent number
US07176202B2

Linked notes

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