Hydrochloric Acid → 2-[3-Methoxy-4-(piperidin-4-yloxy)-phenyl]-5-(6-methoxy-pyridin-3-yl)-imidazo[2,1-b][1,3,4]thiadiazole

HRID 2409547Notes

Reaction equation

HRID 2409547 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[S:25][C:24]4=[N:26][CH:27]=[C:28]([C:29]5[CH:30]=[N:31][C:32]([O:35][CH3:36])=[CH:33][CH:34]=5)[N:23]4[N:22]=3)=[CH:17][C:16]=2[O:37][CH3:38])[CH2:10][CH2:9]1)=O)(C)(C)C.Cl>C(Cl)Cl>[CH3:38][O:37][C:16]1[CH:17]=[C:18]([C:21]2[S:25][C:24]3=[N:26][CH:27]=[C:28]([C:29]4[CH:30]=[N:31][C:32]([O:35][CH3:36])=[CH:33][CH:34]=4)[N:23]3[N:22]=2)[CH:19]=[CH:20][C:15]=1[O:14][CH:11]1[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 667171514-{2-Methoxy-4-[5-(6-methoxy-pyridin-3-yl)-imidazo[2,1-b][1,3,4]thiadiazol-2-yl]-phenoxy}-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 469411272-[3-Methoxy-4-(piperidin-4-yloxy)-phenyl]-5-(6-methoxy-pyridin-3-yl)-imidazo[2,1-b][1,3,4]thiadiazoleYield 100.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4-{2-Methoxy-4-[5-(6-methoxy-pyridin-3-yl)-imidazo[2,1-b][1,3,4]thiadiazol-2-yl]-phenoxy}-piperidine-1-carboxylic acid tert-butyl ester (11 mg; 0.0204 mmol; 1 eq) was dissolved in anhydrous DCM (1 ml) and 4M HCl (0.051 ml, 0.204 mmol, 10 eq) was added. The reaction mixture was stirred at RT for 2 h. The excess of acid was co-evaporated with DCM (×3) to give the desired product (9 mg, 100%) as a white solid. HPLC-MS (5-100% B in 8 min at 0.8 mL): tR=3.24 min, [M+H]+ m/z 438.2; 1H NMR (300 MHz, MeOD) δ 8.98 (s, 1H), 8.54 (m, 1H), 8.25 (m, 1H), 7.66 (m, 2H), 7.28 (m, 2H), 4.76 (m, 1H), 4.10 (s, 3H), 3.94 (s, 3H), 3.45 (m, 2H), 3.21 (m, 2H), 2.17 (m, 4H).

Sources & evidence

ORD record
ord-3fe9ad4deb4e4944944b8bbc750f17b2
Source dataset
uspto-grants-2014_08
Patent number
US08815918B2

Reaction notes

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