1,2-Dichloroethane → HCID 41507106, compound

HRID 1522376Notes

Reaction equation

HRID 1522376 reaction equation
[CH3:1][CH:2]([N:4]1[C:8]2[N:9]=[C:10]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:11]=[C:12]([C:13]([OH:15])=O)[C:7]=2[CH:6]=[N:5]1)[CH3:3].[NH2:22][CH2:23][C:24]1[C:25](=[O:32])[NH:26][C:27]([CH3:31])=[CH:28][C:29]=1[CH3:30].Cl.ON1C2N=CC=CC=2N=N1.CN1CCOCC1.C(Cl)CCl>CS(C)=O.O>[CH3:30][C:29]1[CH:28]=[C:27]([CH3:31])[NH:26][C:25](=[O:32])[C:24]=1[CH2:23][NH:22][C:13]([C:12]1[C:7]2[CH:6]=[N:5][N:4]([CH:2]([CH3:3])[CH3:1])[C:8]=2[N:9]=[C:10]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:11]=1)=[O:15]

Participants

9

Reactant 6

HCID 111,2-DichloroethaneHCID 313Hydrochloric AcidHCID 79724-MethylmorpholineHCID 181649HOAtHCID 25350531-(1-Methylethyl)-6-phenyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acidHCID 70638443-(Aminomethyl)-4,6-dimethyl-1,2-dihydropyridin-2-one

Product 1

HCID 41507106HCID 41507106, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

In a 25 mL sealable tube under nitrogen were combined 1-(1-methylethyl)-6-phenyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (70 mg, 0.25 mmol) and 3-(aminomethyl)-4,6-dimethyl-2(1H)-pyridinone.HCl (56.3 mg, 0.3 mmol) in DMSO (3 mL). 1-hydroxy-7-azabenzotriazole (51 mg, 0.37 mmol) was added and the resulting mixture was degassed with nitrogen for 10 min. N-methylmorpholine (0.1 ml, 0.87 mmol) and EDC (72 mg, 0.37 mmol) were added, the vessel was sealed, and the bright yellow mixture was stirred at room temperature for 2 days. Next added 2 mL of water, and the contents were stirred for 10 min. Solids that precipitated were sonicated, and allowed to stand at room temperature for 10 min. The reaction contents were filtered and washed with water. The solid was treated with 2 mL of EtOH, sonicated and heated, and then allowed to cool to room temperature. The contents were filtered, washed with water and dried to afford the title compound (74 mg, 70%) as a white solid. LCMS E-S (M+H)=416.3. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.58 (s, 1 H), 8.98 (t, J=4.80 Hz, 1 H), 8.38 (s, 1 H), 8.25-8.30 (m, 2 H), 8.17 (s, 1 H), 7.49-7.59 (m, 3 H), 5.91 (s, 1 H), 5.30-5.38 (m, 1 H), 4.42 (d, J=4.80 Hz, 2 H), 2.23 (s, 3 H), 2.13 (s, 3 H), 1.55 (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 min
  3. customthe vessel was sealed
  4. stirringthe contents were stirred for 10 min
  5. customSolids that precipitated
  6. customwere sonicated
  7. waitto stand at room temperature for 10 min
  8. customThe reaction contents
  9. filtrationwere filtered
  10. washwashed with water
  11. additionThe solid was treated with 2 mL of EtOH
  12. customsonicated
  13. temperatureheated
  14. temperatureto cool to room temperature
  15. filtrationThe contents were filtered
  16. washwashed with water
  17. customdried

Sources & evidence

ORD record
ord-603b184fa1f64ceab7f16f221c2e6145
Source dataset
uspto-grants-2015_07
Patent number
US09073924B2

Reaction notes

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