1,2-Dichloroethane → HCID 56599078, compound

HRID 1522468Notes

Reaction equation

HRID 1522468 reaction equation
[CH:1]1([C:4]2[CH:5]=[C:6]([C:21](O)=[O:22])[C:7]3[C:12]([CH3:13])=[N:11][N:10]([CH:14]4[CH2:19][CH2:18][N:17]([CH3:20])[CH2:16][CH2:15]4)[C:8]=3[N:9]=2)[CH2:3][CH2:2]1.[NH2:24][CH2:25][C:26]1[C:27](=[O:34])[NH:28][C:29]([CH3:33])=[CH:30][C:31]=1[CH3:32].ON1C2N=CC=CC=2N=N1.C(Cl)CCl.CN1CCOCC1>CS(C)=O.O>[CH:1]1([C:4]2[CH:5]=[C:6]([C:21]([NH:24][CH2:25][C:26]3[C:27](=[O:34])[NH:28][C:29]([CH3:33])=[CH:30][C:31]=3[CH3:32])=[O:22])[C:7]3[C:12]([CH3:13])=[N:11][N:10]([CH:14]4[CH2:15][CH2:16][N:17]([CH3:20])[CH2:18][CH2:19]4)[C:8]=3[N:9]=2)[CH2:2][CH2:3]1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 181649HOAtHCID 70638443-(Aminomethyl)-4,6-dimethyl-1,2-dihydropyridin-2-oneHCID 67124533HCID 67124533, compound

Product 1

HCID 56599078HCID 56599078, compoundYield 9.3%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

6-Cyclopropyl-3-methyl-1-(1-methyl-4-piperidinyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (150 mg, 0.477 mmol), 3-(aminomethyl)-4,6-dimethyl-2(1H)-pyridinone (117 mg, 0.620 mmol), 1-hydroxy-7-azabenzotriazole (130 mg, 0.954 mmol), EDC (183 mg, 0.954 mmol) and N-methylmorpholine (0.210 mL, 1.909 mmol) were suspended in DMSO(10 mL) and stirred at room temperature for 16 h. Next was added 25 mL of water, stirred for 10 minutes, and then extracted with EtOAc (5×). The organic layers were concentrated in vacuo to afford 20 mg product. The aqueous phase was concentrated in vacuo and the crude residue purified by reverse phase HPLC (mobile phase: 10-60% ACN in H2O, 0.1% NH4OH) to afford additional product. The final product was collected as a solid, 0.100 g (47%). LCMS E-S (M+H)=449.0. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.97-1.05 (m, 4 H), 1.79 (d, J=9.60 Hz, 2 H), 2.11 (s, 3 H), 2.15 (d, J=8.34 Hz, 3 H), 2.21 (s, 3 H), 2.23-2.27 (m, 3 H), 2.35 (s, 3 H), 2.91 (d, J=8.08 Hz, 2 H), 4.33 (d, J=4.80 Hz, 2 H), 4.49-4.72 (m, 1 H), 5.86 (s, 1 H), 6.97 (s, 1 H), 6.92-7.07 (m, 1 H), 8.58 (t, J=4.93 Hz, 1 H), 11.50 (s, 1 H).

Workup

  1. stirringstirred for 10 minutes
  2. extractionextracted with EtOAc (5×)
  3. concentrationThe organic layers were concentrated in vacuo

Sources & evidence

ORD record
ord-9c9a5c307d3e4e659510eb558a339b45
Source dataset
uspto-grants-2015_07
Patent number
US09073924B2

Reaction notes

Loading…