Hydrochloric Acid → Hydrochloric Acid

HRID 2409576Notes

Reaction equation

HRID 2409576 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11]2([C:21]3[C:16](=[CH:17][CH:18]=[C:19]([C:22]4[S:26][C:25]5=[N:27][CH:28]=[C:29]([C:30]6[CH:31]=[C:32]([C:37]([F:40])([F:39])[F:38])[C:33]([NH2:36])=[N:34][CH:35]=6)[N:24]5[N:23]=4)[CH:20]=3)[NH:15][C:14]2=[O:41])[CH2:10][CH2:9]1)=O)(C)(C)C.[ClH:42]>CO>[O:41]=[C:14]1[C:11]2([CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([C:22]3[S:26][C:25]4=[N:27][CH:28]=[C:29]([C:30]5[CH:31]=[C:32]([C:37]([F:38])([F:40])[F:39])[C:33]([NH2:36])=[N:34][CH:35]=5)[N:24]4[N:23]=3)[CH:20]=2)[NH:15]1.[ClH:42]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67284974HCID 67284974, compound

Product 2

HCID 313Hydrochloric AcidYield 1,246.7%HCID 66716818HCID 66716818, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 5-[2-(1′-(tert-butoxycarbonyl)-2-oxo-1,2-dihydrospiro[indole-3,4′-piperidine]-5-yl)-imidazo[2,1-b][1,3,4]thiadiazol-5-yl]-3-trifluoromethyl-pyridin-2-ylamine (6.4 mg, 0.011 mmol) and HCl (4N in dioxane, 0.03 mL, 0.11 mmol) in MeOH (0.2 mL) was stirred at room temperature for 16 h. The solvent was evaporated under vacuum and the residue was triturated from Et2O to give the desired product as HCl salt (5 mg, 86%). HPLC-MS (5-100% B in 8 min at 0.8 mL): tR=3.01 min, [M+H]+ m/z 486.1; 1H NMR (300 MHz, D2O) δ 8.19 (m, 1H), 8.04 (m, 1H), 7.31 (m, 3H), 6.56 (m, 1H), 3.49 (m, 2H), 3.21 (m, 2H), 3.10 (m, 2H), 1.92 (m, 2H), 1.72 (m, 2H).

Workup

  1. customThe solvent was evaporated under vacuum
  2. customthe residue was triturated from Et2O

Sources & evidence

ORD record
ord-054c6b9dcf04499d935dd5ff3efc6132
Source dataset
uspto-grants-2014_08
Patent number
US08815918B2

Reaction notes

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