1,2-Dichloroethane → 1-Amino-6-cyclopropyl-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1H-pyrazolo[3,4-b]pyridine-4-carboxamide

HRID 1522461Notes

Reaction equation

HRID 1522461 reaction equation
[NH2:1][N:2]1[C:6]2[N:7]=[C:8]([CH:14]3[CH2:16][CH2:15]3)[CH:9]=[C:10]([C:11]([OH:13])=O)[C:5]=2[CH:4]=[N:3]1.[NH2:17][CH2:18][C:19]1[C:20](=[O:27])[NH:21][C:22]([CH3:26])=[CH:23][C:24]=1[CH3:25].ON1C2N=CC=CC=2N=N1.C(Cl)CCl.CN1CCOCC1>CS(C)=O>[NH2:1][N:2]1[C:6]2[N:7]=[C:8]([CH:14]3[CH2:16][CH2:15]3)[CH:9]=[C:10]([C:11]([NH:17][CH2:18][C:19]3[C:20](=[O:27])[NH:21][C:22]([CH3:26])=[CH:23][C:24]=3[CH3:25])=[O:13])[C:5]=2[CH:4]=[N:3]1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 181649HOAtHCID 70638443-(Aminomethyl)-4,6-dimethyl-1,2-dihydropyridin-2-oneHCID 671242951-Amino-6-cyclopropyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid

Product 1

HCID 680785871-Amino-6-cyclopropyl-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1H-pyrazolo[3,4-b]pyridine-4-carboxamide

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

The title compound was prepared in the same manner as described for intermediate 56 using 1-amino-6-cyclopropyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (73 mg, 0.335 mmol), 3-(aminomethyl)-4,6-dimethyl-2(1H)-pyridinone (76 mg, 0.502 mmol), 1-hydroxy-7-azabenzotriazole (91 mg, 0.669 mmol), DMSO(10 mL), EDC (128 mg, 0.669 mmol), and N-methylmorpholine (0.147 mL, 1.338 mmol). The aq. phase was extracted with EtOAc (5×30 mL). The combined EtOAc extracts were dried over MgSO4, filtered, and concentrated in vacuo. The final product was collected as 0.068 g (58%). LCMS E-S (M+H)=353.3. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.99-1.14 (m, 4 H), 2.13 (s, 3 H), 2.22 (s, 4 H), 4.35 (d, J=4.80 Hz, 2 H), 5.90 (s, 1 H), 6.31 (s, 2 H), 7.41 (s, 1 H), 8.04 (s, 1 H), 8.74 (s, 1 H), 11.58 (br. s., 1 H).

Workup

  1. extractionThe aq. phase was extracted with EtOAc (5×30 mL)
  2. dry with materialThe combined EtOAc extracts were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe final product was collected as 0.068 g (58%)

Sources & evidence

ORD record
ord-e07d3ed7109a4388a98d9e840d7bd9e7
Source dataset
uspto-grants-2015_07
Patent number
US09073924B2

Reaction notes

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