1,2-Dichloroethane → HCID 89467176, compound

HRID 1522532Notes

Reaction equation

HRID 1522532 reaction equation
[CH:1]1([N:4]2[C:8]3[N:9]=[C:10]([CH:16]4[CH2:18][CH2:17]4)[CH:11]=[C:12]([C:13]([OH:15])=O)[C:7]=3[C:6]([CH3:19])=[N:5]2)[CH2:3][CH2:2]1.[NH2:20][CH2:21][C:22]1[C:23](=[O:32])[NH:24][C:25]([CH3:31])=[CH:26][C:27]=1[CH2:28][CH2:29][CH3:30].ON1C2N=CC=CC=2N=N1.C(Cl)CCl.CN1CCOCC1>CS(C)=O.O>[CH:1]1([N:4]2[C:8]3[N:9]=[C:10]([CH:16]4[CH2:18][CH2:17]4)[CH:11]=[C:12]([C:13]([NH:20][CH2:21][C:22]4[C:23](=[O:32])[NH:24][C:25]([CH3:31])=[CH:26][C:27]=4[CH2:28][CH2:29][CH3:30])=[O:15])[C:7]=3[C:6]([CH3:19])=[N:5]2)[CH2:2][CH2:3]1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 181649HOAtHCID 671241403-(Aminomethyl)-6-methyl-4-propylpyridin-2(1H)-oneacetateHCID 89444908HCID 89444908, compound

Product 1

HCID 89467176HCID 89467176, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

1,6-dicyclopropyl-3-methyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (125 mg, 0.486 mmol), 3-(aminomethyl)-6-methyl-4-propyl-2(1H)-pyridinone (126 mg, 0.583 mmol), 1-hydroxy-7-azabenzotriazole (132 mg, 0.972 mmol), EDC (186 mg, 0.972 mmol) and N-methylmorpholine (0.214 mL, 1.943 mmol) were suspended in Dimethyl Sulfoxide (DMSO) (10 mL) and stirred at room temperature for 16 hours. Added 25 mL of water and let stir for 10 minutes. The contents were filtered and dried. The product was collected as 200 mg. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.92 (t, J=7.07 Hz, 3 H), 1.04 (d, J=6.06 Hz, 8 H), 1.45-1.73 (m, 2 H), 2.12 (s, 3 H), 2.24 (br. s., 1 H), 2.33 (s, 3 H), 3.79 (br. s., 1 H), 4.34 (d, J=3.79 Hz, 2 H), 5.89 (br. s., 1 H), 6.99 (s, 1 H), 8.57 (br. s., 1 H), 11.51 (br. s., 1 H). MS(ES) [M+H]+ 420.2

Workup

  1. stirringlet stir for 10 minutes
  2. filtrationThe contents were filtered
  3. customdried
  4. customThe product was collected as 200 mg

Sources & evidence

ORD record
ord-0e60bd9aa7ac4130a76124cab4c4ad5a
Source dataset
uspto-grants-2015_07
Patent number
US09073924B2

Reaction notes

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