1,2-Dichloroethane → HCID 17393134, compound

HRID 1522375Notes

Reaction equation

HRID 1522375 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:14]([OH:16])=O)[C:5]2[CH:10]=[N:9][N:8]([CH:11]([CH3:13])[CH3:12])[C:6]=2[N:7]=1.[NH2:17][CH2:18][C:19]1[C:20](=[O:27])[NH:21][C:22]([CH3:26])=[CH:23][C:24]=1[CH3:25].Cl.ON1C2N=CC=CC=2N=N1.CN1CCOCC1.C(Cl)CCl>CS(C)=O.O>[CH3:25][C:24]1[CH:23]=[C:22]([CH3:26])[NH:21][C:20](=[O:27])[C:19]=1[CH2:18][NH:17][C:14]([C:4]1[C:5]2[CH:10]=[N:9][N:8]([CH:11]([CH3:12])[CH3:13])[C:6]=2[N:7]=[C:2]([CH3:1])[CH:3]=1)=[O:16]

Participants

9

Reactant 6

HCID 111,2-DichloroethaneHCID 313Hydrochloric AcidHCID 79724-MethylmorpholineHCID 181649HOAtHCID 65042191-isopropyl-6-methyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid(SALTDATA: FREE)HCID 70638443-(Aminomethyl)-4,6-dimethyl-1,2-dihydropyridin-2-one

Product 1

HCID 17393134HCID 17393134, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

In a 25 mL sealable tube under nitrogen were combined 6-methyl-1-(1-methylethyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (60 mg, 0.27 mmol) and 3-(aminomethyl)-4,6-dimethyl-2(1H)-pyridinone.HCl (62 mg, 0.33 mmol) in DMSO (3 mL). 1-hydroxy-7-azabenzotriazole (56 mg, 0.41 mmol) was added and the resulting mixture was degassed with nitrogen for 10 minutes. N-methylmorpholine (0.11 ml, 0.96 mmol) and EDC (79 mg, 0.41 mmol) were added, the vessel was sealed, and the light brown mixture was stirred at room temperature for 2 days. Next added 2 mL of water and the mixture was stirred for 10 min. Solids that precipitated were sonicated, and allowed to stand at room temperature for 10 min. The contents were filtered, washed with water, and dried to afford the title compound (68 mg, 68%) as a light pink solid. LCMS E-S (M+H)=354.3. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.54 (s, 1 H), 8.69 (t, J=4.80 Hz, 1 H), 8.26 (s, 1 H), 7.46 (s, 1 H), 5.89 (s, 1 H), 5.20 (quin, J=6.69 Hz, 1 H), 4.36 (d, J=5.05 Hz, 2 H), 2.63 (s, 3 H), 2.21 (s, 3 H), 2.13 (s, 3 H), 1.48 (d, J=6.57 Hz, 6 H).

Workup

  1. customIn a 25 mL sealable tube under nitrogen were combined
  2. customthe resulting mixture was degassed with nitrogen for 10 minutes
  3. customthe vessel was sealed
  4. stirringthe mixture was stirred for 10 min
  5. customSolids that precipitated
  6. customwere sonicated
  7. waitto stand at room temperature for 10 min
  8. filtrationThe contents were filtered
  9. washwashed with water
  10. customdried

Sources & evidence

ORD record
ord-399ce44d0d934ebba8072d86dc29d121
Source dataset
uspto-grants-2015_07
Patent number
US09073924B2

Reaction notes

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