1,2-Dichloroethane → HCID 56598944, compound

HRID 1522460Notes

Reaction equation

HRID 1522460 reaction equation
[CH:1]1([C:4]2[CH:5]=[C:6]([C:17](O)=[O:18])C3C=NN(CC(C)C)C=3[N:9]=2)[CH2:3][CH2:2]1.[NH2:20][CH2:21][C:22]1[C:23](=[O:30])[NH:24][C:25]([CH3:29])=[CH:26][C:27]=1[CH3:28].O[N:32]1[C:36]2N=CC=C[C:35]=2N=N1.[CH2:41](Cl)CCl.C[N:46]1[CH2:51][CH2:50]O[CH2:48][CH2:47]1>CS(C)=O>[CH:1]1([C:4]2[CH:5]=[C:6]([C:17]([NH:20][CH2:21][C:22]3[C:23](=[O:30])[NH:24][C:25]([CH3:29])=[CH:26][C:27]=3[CH3:28])=[O:18])[C:50]3[C:36]([CH3:35])=[N:32][N:46]([CH:47]([CH3:48])[CH3:41])[C:51]=3[N:9]=2)[CH2:3][CH2:2]1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 181649HOAtHCID 70638443-(Aminomethyl)-4,6-dimethyl-1,2-dihydropyridin-2-oneHCID 16792462HCID 16792462, compound

Product 1

HCID 56598944HCID 56598944, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

The title compound was prepared in the same manner as described for intermediate 56 using 6-cyclopropyl-1-(2-methylpropyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (80 mg, 0.309 mmol), 3-(aminomethyl)-4,6-dimethyl-2(1H)-pyridinone (70.4 mg, 0.463 mmol), 1-hydroxy-7-azabenzotriazole (84 mg, 0.617 mmol), DMSO(10 mL), EDC (118 mg, 0.617 mmol), and N-methylmorpholine (0.136 mL, 1.234 mmol). The final product was collected as 0.123 g (100%). LCMS E-S (M+H)=394.2 1H NMR (400 MHz, DMSO-d6) δ ppm 0.93-1.12 (m, 4 H), 1.42 (d, J=6.82 Hz, 6 H), 2.12 (s, 3 H), 2.22 (s, 4 H), 2.36 (s, 3 H), 4.34 (d, J=4.80 Hz, 2 H), 4.90-5.11 (m, 1 H), 5.87 (s, 1 H), 6.99 (s, 1 H), 8.58 (s, 1 H), 11.51 (s, 1 H).

Workup

  1. customThe final product was collected as 0.123 g (100%)

Sources & evidence

ORD record
ord-4d90ab3200f040a1a72b26f2d6af57ca
Source dataset
uspto-grants-2015_07
Patent number
US09073924B2

Reaction notes

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