Hydrochloric Acid → Hydrochloric Acid

HRID 2409545Notes

Reaction equation

HRID 2409545 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]([NH2:39])=[C:33]([C:35]([F:38])([F:37])[F:36])[CH:34]=5)[N:23]4[N:22]=3)=[CH:17][C:16]=2[O:40][CH3:41])[CH2:10][CH2:9]1)=O)(C)(C)C.[ClH:42].O1CCOCC1>C(Cl)Cl>[CH3:41][O:40][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:34]=[C:33]([C:35]([F:37])([F:36])[F:38])[C:32]([NH2:39])=[N:31][CH:30]=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.[ClH:42]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 667171564-{4-[5-(6-Amino-5-trifluoromethyl-pyridin-3-yl)-imidazo[2,1-b][1,3,4]thiadiazol-2-yl]-2-methoxy-phenoxy}-piperidine-1-carboxylic acid tert-butyl ester

Product 2

HCID 313Hydrochloric AcidYield 92%HCID 672843535-{2-[3-Methoxy-4-(piperidin-4-yloxy)-phenyl]-imidazo[2,1-b][1,3,4]thiadiazol-5-yl}-3-trifluoromethyl-pyridin-2-ylamine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-{4-[5-(6-Amino-5-trifluoromethyl-pyridin-3-yl) -imidazo[2,1-b][1,3,4]thiadiazol-2-yl]-2-methoxy-phenoxy}-piperidine-1-carboxylic acid tert-butyl ester (23 mg; 0.039 mmol; 1 eq) was suspended in anhydrous DCM (3 ml) and 4M HCl in 1,4-dioxane (0.097 ml, 0.39 mmol, 10 eq) was added. The reaction mixture was stirred at RT overnight. The solvents were removed and the residue was co-evaporated with DCM (×3). The residue was triturated in CH3CN and filtered to give the desired product as HCl salt (19 mg, 92%). HPLC-MS (5-100% B in 8 min at 0.8 mL): tR=3.25 min, [M+H]+ m/z 491.2; 1H NMR (300 MHz, DMSO) δ 9.10 (s, 2H), 8.88 (s, 1H), 8.49 (d, J=1.6 Hz, 1H), 7.87 (s, 1H), 7.53 (m, 2H), 7.31 (d, J=9.1 Hz, 1H), 4.76 (s, 1H), 3.91 (s, 3H), 3.17 (m, 2H), 3.09 (m, 2H), 2.12 (m, 2H), 1.90 (m, 2H).

Workup

  1. customThe solvents were removed
  2. customThe residue was triturated in CH3CN
  3. filtrationfiltered

Sources & evidence

ORD record
ord-2692ae732b504933be3052af27e94e45
Source dataset
uspto-grants-2014_08
Patent number
US08815918B2

Reaction notes

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