Hydrochloric Acid → Hydrochloric Acid

HRID 2409549Notes

Reaction equation

HRID 2409549 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]([NH2:35])=[N:33][CH:34]=5)[N:23]4[N:22]=3)=[CH:17][C:16]=2[O:36][CH3:37])[CH2:10][CH2:9]1)=O)(C)(C)C.[ClH:38].O1CCOCC1>C(Cl)Cl.CO>[CH3:37][O:36][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]=[N:33][C:32]([NH2:35])=[N:31][CH:30]=4)[N:23]3[N:22]=2)[CH:19]=[CH:20][C:15]=1[O:14][CH:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1.[ClH:38]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 667172554-{4-[5-(2-Amino-pyrimidin-5-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 77%HCID 672839105-{2-[3-Methoxy-4-(piperidin-4-yloxy)-phenyl]-imidazo[2,1-b][1,3,4]thiadiazol-5-yl}-pyrimidin-2-ylamine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

4-{4-[5-(2-Amino-pyrimidin-5-yl)-imidazo[2,1-b][1,3,4]thiadiazol-2-yl]-2-methoxy-phenoxy}-piperidine-1-carboxylic acid tert-butyl ester (9 mg; 0.017 mmol; 1 eq) was dissolved in anhydrous DCM (1 mL) and 4M HCl in 1,4-dioxane (0.042 ml, 0.17 mmol, 10 eq) was added. The reaction mixture was stirred at RT overnight. The solvent was evaporated and the residue was co-evaporated with DCM (×3). The residue was triturated in CH3CN and filtered. The oily-solid obtained was dissolved in MeOH and evaporated to give the desired product as HCl salt (6 mg, 77%). HPLC-MS (5-100% B in 8 min at 0.8 mL): tR=3.29 min, [M+H]+ m/z 424.1; 1H NMR (300 MHz, DMSO) δ 8.93 (s, 3H), 7.77 (s, 1H), 7.55 (m, 2H), 7.29 (d, J=8.9 Hz, 1H), 4.76 (m, 1H), 3.92 (s, 3H), 3.23 (m, 2H), 3.09 (m, 2H), 2.11 (m, 2H), 1.90 (m, 2H).

Workup

  1. customThe solvent was evaporated
  2. customThe residue was triturated in CH3CN
  3. filtrationfiltered
  4. customThe oily-solid obtained
  5. customevaporated

Sources & evidence

ORD record
ord-ff58cd6a30cd4959895f500b61f0fba7
Source dataset
uspto-grants-2014_08
Patent number
US08815918B2

Reaction notes

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