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

HRID 475958Notes

Reaction equation

HRID 475958 reaction equation
[CH3:1][CH:2]([N:4]1[C:8]2[N:9]=[C:10]([C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)[CH:11]=[C:12]([C:13]([OH:15])=O)[C:7]=2[CH:6]=[N:5]1)[CH3:3].[NH2:22][CH2:23][C:24]1[C:25](=[O:33])[NH:26][C:27]([CH2:31][CH3:32])=[CH:28][C:29]=1[CH3:30].C(O)(C(F)(F)F)=O.C1C=NC2N(O)N=NC=2C=1.C(Cl)CCl.CN1CCOCC1>CN(C=O)C>[CH2:31]([C:27]1[NH:26][C:25](=[O:33])[C:24]([CH2:23][NH:22][C:13]([C:12]2[C:7]3[CH:6]=[N:5][N:4]([CH:2]([CH3:1])[CH3:3])[C:8]=3[N:9]=[C:10]([C:16]3[CH:17]=[CH:18][N:19]=[CH:20][CH:21]=3)[CH:11]=2)=[O:15])=[C:29]([CH3:30])[CH:28]=1)[CH3:32]

Participants

8

Reactant 6

HCID 111,2-DichloroethaneHCID 6422Trifluoroacetic acidHCID 79724-MethylmorpholineHCID 181649HOAtHCID 201146251-(1-Methylethyl)-6-(4-pyridinyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acidHCID 67124323HCID 67124323, compound

Product 1

HCID 56597561N-[(6-Ethyl-4-methyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-6-(4-pyridinyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared in the same manner as described in example 9 from 1-(1-methylethyl)-6-(4-pyridinyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (403 mg, 1.427 mmol), 3-(aminomethyl)-6-ethyl-4-methyl-2(1H)-pyridinone.TFA (400 mg, 1.427 mmol), HOAT (291 mg, 2.141 mmol), EDC (1094 mg, 5.71 mmol), N-methylmorpholine (0.628 mL, 5.71 mmol), and DMF (6 mL). The final product was collected as a white solid, 232 mg (38%). LCMS E-S (M+H)=432.4. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.14 (t, 3H), 1.56 (d, J=6.57 Hz, 6H), 2.25 (s, 3H), 2.42 (q, J=7.41 Hz, 2H), 4.43 (d, J=4.55 Hz, 2H), 5.29-5.45 (m, 1H), 5.93 (s, 1H), 8.22 (d, J=6.06 Hz, 2H), 8.30 (s, 1H), 8.45 (s, 1H), 8.78 (d, J=5.81 Hz, 2H), 9.01 (t, J=4.55 Hz, 1H), 11.58 (s, 1H).

Workup

  1. customThe final product was collected as a white solid, 232 mg (38%)

Sources & evidence

ORD record
ord-baa8727d001b4f6982f1071e6ee49eba
Source dataset
uspto-grants-2014_01
Patent number
US08637509B2

Reaction notes

Loading…