Hydrochloric Acid → HCID 66618139, compound

HRID 911097Notes

Reaction equation

HRID 911097 reaction equation
[CH3:1][N:2]([CH3:43])[CH2:3][CH2:4][NH:5][C:6]([C:8]1[C:9]([CH3:42])=[C:10]([O:15][C:16]2[C:21]([Br:22])=[CH:20][N:19]=[C:18]([NH:23][C:24]3[S:28][N:27]=[C:26]([CH:29]4[CH2:34][CH2:33][N:32](C(OC(C)(C)C)=O)[CH2:31][CH2:30]4)[N:25]=3)[CH:17]=2)[C:11]([CH3:14])=[N:12][CH:13]=1)=[O:7].[Cl:44]CCl.[ClH:47]>CO>[ClH:44].[ClH:47].[Br:22][C:21]1[C:16]([O:15][C:10]2[C:11]([CH3:14])=[N:12][CH:13]=[C:8]([C:9]=2[CH3:42])[C:6]([NH:5][CH2:4][CH2:3][N:2]([CH3:1])[CH3:43])=[O:7])=[CH:17][C:18]([NH:23][C:24]2[S:28][N:27]=[C:26]([CH:29]3[CH2:30][CH2:31][NH:32][CH2:33][CH2:34]3)[N:25]=2)=[N:19][CH:20]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 24995282HCID 24995282, compound

Product 1

HCID 66618139HCID 66618139, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

tert-Butyl 4-(5-(4-(5-((2-(dimethylamino)ethyl)carbamoyl)-2,4-dimethylpyridin-3-yloxy)-5-bromopyridin-2-ylamino)-1,2,4-thiadiazol-3-yl)piperidine-1-carboxylate (0.025 g, 0.037 mmol) was dissolved in a mixture of methanol:dichloromethane (1 mL each). HCl (4N in dioxane, 0.5 mL, 2.0 mmol) was added. The reaction stirred overnight. The solution was concentrated to give 5-(5-bromo-2-(3-(piperidin-4-yl)-1,2,4-thiadiazol-5-ylamino)pyridin-4-yloxy)-N-(2-(dimethylamino)ethyl)-4,6-dimethylnicotin-amide dihydrochloride (0.028 g, 100% yield) as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ 1.87-1.93 (m, 2H), 2.06-2.14 (m, 2H), 2.22 (s, 3H), 2.34 (s, 3H), 2.83 (s, 3H), 2.84 (s, 3H), 2.96-3.08 (m, 2H), 3.23-3.32 (m, 4H), 3.44-2.52 (m, 1H), 3.62-3.73 (m, 2H), 6.37 (s, 1H), 8.64 (s, 1H), 8.67 (s, 1H), 8.70 (s, 1H), 9.0 (s, 1H), 9.03 (t, 1H), 10.50 (s, 1H), 11.88 (s, 1H).

Workup

  1. concentrationThe solution was concentrated

Sources & evidence

ORD record
ord-8b52914f29ef4f8a894f507a118e2d17
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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