1,2-Dichloroethane → HCID 89444901, compound

HRID 1522524Notes

Reaction equation

HRID 1522524 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:15]([OH:17])=O)[C:5]2[C:10]([CH3:11])=[N:9][N:8]([CH:12]3[CH2:14][CH2:13]3)[C:6]=2[N:7]=1.[NH2:18][CH2:19][C:20]1[C:21](=[O:28])[NH:22][C:23]([CH3:27])=[CH:24][C:25]=1[CH3:26].ON1C2N=CC=CC=2N=N1.C(Cl)CCl.CN1CCOCC1>CS(C)=O.O>[Cl:1][C:2]1[CH:3]=[C:4]([C:15]([NH:18][CH2:19][C:20]2[C:21](=[O:28])[NH:22][C:23]([CH3:27])=[CH:24][C:25]=2[CH3:26])=[O:17])[C:5]2[C:10]([CH3:11])=[N:9][N:8]([CH:12]3[CH2:13][CH2:14]3)[C:6]=2[N:7]=1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 181649HOAtHCID 70638443-(Aminomethyl)-4,6-dimethyl-1,2-dihydropyridin-2-oneHCID 89544017HCID 89544017, compound

Product 1

HCID 89444901HCID 89444901, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

6-chloro-1-cyclopropyl-3-methyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (297 mg, 1.180 mmol), 3-(aminomethyl)-4,6-dimethyl-2(1H)-pyridinone (289 mg, 1.534 mmol), 1-hydroxy-7-azabenzotriazole (321 mg, 2.360 mmol), EDC (452 mg, 2.360 mmol) and N-methylmorpholine (0.519 mL, 4.72 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 455 mg. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.01-1.22 (m, 4 H), 2.12 (s, 3 H), 2.22 (s, 3 H), 2.36 (s, 3 H), 3.74-3.87 (m, 1 H), 4.33 (d, J=5.05 Hz, 2 H), 5.88 (s, 1 H), 7.19 (s, 1 H), 8.79 (t, J=4.67 Hz, 1 H), 11.53 (br. s., 1 H). MS(ES) [M+H]+385.9

Workup

  1. stirringlet stir for 10 minutes
  2. filtrationThe contents were filtered
  3. customdried
  4. customThe product was collected as 455 mg

Sources & evidence

ORD record
ord-0455b7a49c16406b9680ed943768fd6c
Source dataset
uspto-grants-2015_07
Patent number
US09073924B2

Reaction notes

Loading…