1,2-Dichloroethane → HCID 67345799, compound

HRID 1678802Notes

Reaction equation

HRID 1678802 reaction equation
Cl.[CH3:2][C:3]1[N:15]2[C:6]([C:7]3[CH:8]=[C:9]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[C:10]([C:16]4[CH:21]=[CH:20][C:19]([CH2:22][NH2:23])=[CH:18][CH:17]=4)=[N:11][C:12]=3[CH:13]=[CH:14]2)=[N:5][N:4]=1.C(Cl)C[Cl:32].C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.Cl.[N:54]1[CH:59]=[CH:58][CH:57]=[C:56]([CH2:60][C:61](O)=[O:62])[CH:55]=1>CN(C)C=O>[Cl-:32].[CH3:2][C:3]1[N:15]2[C:6]([C:7]3[CH:8]=[C:9]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[C:10]([C:16]4[CH:17]=[CH:18][C:19]([CH2:22][NH:23][C:61](=[O:62])[CH2:60][C:56]5[CH:55]=[NH+:54][CH:59]=[CH:58][CH:57]=5)=[CH:20][CH:21]=4)=[N:11][C:12]=3[CH:13]=[CH:14]2)=[N:5][N:4]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27237243-Pyridineacetic acid, hydrochloride (1:1)HCID 68668700HCID 68668700, compound

Product 1

HCID 67345799HCID 67345799, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To 1-[4-(3-methyl-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)phenyl]methanamine hydrochloride (5-3, 20 mg, 0.050 mmol)), EDC (12 mg, 0.065 mmol), HOBT (10 mg, 0.0650 mmol), DIPEA (0.033 ml, 0.199 mmol), and pyridin-3-ylacetic acid hydrochloride (11 mg, 0.0650 mmol) was added 0.6 mL anhydrous dimethylformamide. The reaction mixture was then heated under microwave irradiation at 100° C. for 5 minutes. Purification of crude reaction mixture by reverse phase chromatography (Waters Sunfire MSC18, 1% acetonitrile/0.1% trifluoroacetic acid/water→95% acetonitrile/0.1% trifluoroacetic acid/water) & conversion to HCl salt (addition of saturated solution of HCl in ethyl acetate (˜4N) & concentration) gave the title compound as yellow solid. HRMS (M+H+): calculated=243.1079, observed=243.1083.

Workup

  1. customPurification of crude
  2. customreaction mixture by reverse phase chromatography (Waters Sunfire MSC18, 1% acetonitrile/0.1% trifluoroacetic acid/water→95% acetonitrile/0.1% trifluoroacetic acid/water) & conversion to HCl salt (addition of saturated solution of HCl in ethyl acetate (˜4N) & concentration)

Sources & evidence

ORD record
ord-e161e5b7445f431881ab63a89c1a8df7
Source dataset
uspto-grants-2011_08
Patent number
US08008317B2

Reaction notes

Loading…