1,2-Dichloroethane → HCID 54597075, compound

HRID 1476426Notes

Reaction equation

HRID 1476426 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:16]([OH:18])=O)[C:5]2[CH:6]=[N:7][N:8]([CH:11]3[CH2:15][CH2:14][CH2:13][CH2:12]3)[C:9]=2[CH:10]=1.[NH2:19][CH2:20][C:21]1[C:22](=[O:30])[NH:23][C:24]([CH3:29])=[CH:25][C:26]=1[CH2:27][CH3:28].Cl.ON1C2N=CC=CC=2N=N1.CN1CCOCC1.C(Cl)CCl.C([O-])([O-])=O.[K+].[K+]>CS(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([C:16]([NH:19][CH2:20][C:21]2[C:22](=[O:30])[NH:23][C:24]([CH3:29])=[CH:25][C:26]=2[CH2:27][CH3:28])=[O:18])[C:5]2[CH:6]=[N:7][N:8]([CH:11]3[CH2:12][CH2:13][CH2:14][CH2:15]3)[C:9]=2[CH:10]=1

Participants

9

Reactant 7

HCID 111,2-DichloroethaneHCID 313Hydrochloric AcidHCID 79724-MethylmorpholineHCID 11430Potassium CarbonateHCID 181649HOAtHCID 674665833-(aminomethyl)-4-ethyl-6-methylpyridin-2(1H)-oneHCID 674684486-bromo-1-cyclopentyl-1H-indazole-4-carboxylic acid

Product 1

HCID 54597075HCID 54597075, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

In a 25 mL sealable tube under nitrogen were combined 6-bromo-1-cyclopentyl-1H-indazole-4-carboxylic acid (370 mg, 1.2 mmol) and 3-(aminomethyl)-4-ethyl-6-methyl-2(1H)-pyridinone.HCl (340 mg, 1.68 mmol) in DMSO (3 mL). 1-hydroxy-7-azabenzotriazole (277 mg, 2.04 mmol) was added and the resulting mixture was degassed with nitrogen for 10 minutes. N-methylmorpholine (0.55 ml, 5 mmol) and EDC (390 mg, 2 mmol) were added, the vessel was sealed, and the mixture was stirred at room temperature overnight. The mixture was poured onto 10 mL of ice-water and solids crashed out. 10% K2CO3 was added to adjust the pH˜8-9. The mixture was stirred for 4 hours and then allowed to stand for another 2 hours. Solids were filtered and air-dried. DMF along with some water was then added. Solids that precipitated were filtered and dried to afford the title compound as a light orange solid (515 mg, 91%). 1H NMR (400 MHz, DMSO-d6) δ ppm 11.54 (s, 1H) 8.63 (t, J=4.80 Hz, 1H) 8.36 (s, 1H) 8.20 (s, 1H) 7.70 (d, J=1.52 Hz, 1H) 5.93 (s, 1H) 5.23 (t, J=7.07 Hz, 1H) 4.36 (s, 1H) 4.35 (s, 1H) 2.53-2.59 (m, 2H) 2.14 (s, 3H) 2.07-2.13 (m, 2H) 1.93-2.01 (m, 2H) 1.83-1.91 (m, 2H) 1.65-1.73 (m, 2H) 1.10 (t, J=7.58 Hz, 3H); LC-MS (ES) m/z=456.9/459.1

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 4 hours
  5. waitto stand for another 2 hours
  6. filtrationSolids were filtered
  7. customair-dried
  8. additionDMF along with some water was then added
  9. customSolids that precipitated
  10. filtrationwere filtered
  11. customdried

Sources & evidence

ORD record
ord-7af6bad07ef143c2818a694dd0092b76
Source dataset
uspto-grants-2015_04
Patent number
US09018382B2

Reaction notes

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