Hydrochloric Acid → Hydrochloric Acid

HRID 2409559Notes

Reaction equation

HRID 2409559 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:19]([C:20]([F:23])([F:22])[F:21])=[CH:18][C:17]([C:24]3[N:31]4[C:27]([S:28][C:29]([C:32]5[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[C:34]([O:40][CH3:41])[CH:33]=5)=[N:30]4)=[N:26][CH:25]=3)=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[ClH:42]>O1CCOCC1>[CH3:41][O:40][C:34]1[CH:33]=[C:32]([C:29]2[S:28][C:27]3=[N:26][CH:25]=[C:24]([C:17]4[CH:16]=[N:15][C:14]([N:11]5[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]5)=[C:19]([C:20]([F:22])([F:23])[F:21])[CH:18]=4)[N:31]3[N:30]=2)[CH:37]=[CH:36][C:35]=1[O:38][CH3:39].[ClH:42]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 672838244-{5-[2-(3,4-Dimethoxy-phenyl)-imidazo[2,1-b][1,3,4]thiadiazol-5-yl]-3-trifluoromethyl-pyridin-2-yl}-piperazine-1-carboxylic acid tert-butyl ester

Product 2

HCID 313Hydrochloric AcidYield 100%HCID 667169522-(3,4-Dimethoxy-phenyl)-5-(6-piperazin-1-yl-5-trifluoromethyl-pyridin-3-yl)-imidazo[2,1-b][1,3,4]thiadiazole

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of 4-{5-[2-(3,4-Dimethoxy-phenyl)-imidazo[2,1-b][1,3,4]thiadiazol-5-yl]-3-trifluoromethyl-pyridin-2-yl}-piperazine-1-carboxylic acid tert-butyl ester (0.15 g, 0.254 mmol, 1 eq) in dioxane (4 mL) was added an excess of 4M HCl in dioxane (20 eq) at 0° C. The reaction was allowed to warm to rt and it was stirred for 6.5 h. Solvents were removed under reduced pressure to afford the desired product as HCl salt (146 mg, 100%). HPLC-MS: (5-40% B in 8 min, 0.8 mL/min, 50° C.): tR=5.65 min and 5.96 min, [M+H]+ m/z 491.2; 1H NMR (300 MHz, DMSO) δ 9.24 (d, J=1.9 Hz, 1H), 8.77 (d, J=2.1 Hz, 1H), 8.03 (s, 1H), 7.56 (dd, J=8.4, 1.9 Hz, 1H), 7.50 (d, J=1.9 Hz, 1H), 7.19 (d, J=8.5 Hz, 1H), 3.88 (s, 3H), 3.85 (s, 3H), 3.45 (m, 4H), 3.24 (m, 4H).

Workup

  1. customSolvents were removed under reduced pressure

Sources & evidence

ORD record
ord-3ebf27c0f195479c8bb7468fe9d58151
Source dataset
uspto-grants-2014_08
Patent number
US08815918B2

Reaction notes

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