Sodium Bicarbonate → HCID 178479555, compound

HRID 1508740Notes

Reaction equation

HRID 1508740 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([C:9]2[N:14]=[C:13]3[CH2:15][CH2:16][CH2:17][C:12]3=[C:11]([NH:18][C@H:19]3[CH2:24][CH2:23][C@H:22]([CH2:25][C:26]#[N:27])[CH2:21][CH2:20]3)[CH:10]=2)[CH:6]=[CH:7][CH:8]=1.C([O-])(O)=[O:29].[Na+]>S(=O)(=O)(O)O>[ClH:2].[Cl:2][C:3]1[CH:4]=[C:5]([C:9]2[N:14]=[C:13]3[CH2:15][CH2:16][CH2:17][C:12]3=[C:11]([NH:18][C@H:19]3[CH2:24][CH2:23][C@H:22]([CH2:25][C:26]([NH2:27])=[O:29])[CH2:21][CH2:20]3)[CH:10]=2)[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 178479211HCID 178479211, compound

Product 1

HCID 178479555HCID 178479555, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

Trans-2-(4-((2-(3-chlorophenyl)-6,7-dihydro-5H-cyclopenta[b]pyridin-4-yl)amino)cyclohexyl)acetonitrile hydrochloride (0.056 g, 0.14 mmol) was suspended in sulfuric acid (2 mL) at 0° C. The reaction was warmed to rt and stirred for 16 h. After this time, the mixture was added dropwise to a saturated NaHCO3 solution, extracted with ethyl acetate, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated. The residue was purified by column chromatography (silica, dichloromethane/methanol), followed by formation of the hydrochloride salt to afford the title compound (0.048 g, 82%) as a white solid. MW=420.38. 1H NMR (DMSO-d6, 500 MHz) δ 13.50 (s, 1H), 7.99-7.96 (m, 1H), 7.86-7.82 (m, 1H), 7.71-7.67 (m, 1H), 7.62-7.58 (m, 2H), 7.27 (s, 1H), 7.10 (s, 1H), 6.73 (s, 1H), 3.89-3.79 (m, 1H), 3.06 (t, J=7.5 Hz, 2H), 2.78 (t, J=7.5 Hz, 2H), 2.17 (quin, J=7.5 Hz, 2H), 1.96 (d, J=7.0 Hz, 2H), 1.92-1.85 (m, 2H), 1.78-1.71 (m, 2H), 1.70-1.60 (m, 1H), 1.50-1.38 (m, 2H), 1.21-1.09 (m, 1H); APCI MS m/z 384 [M+H]+.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated
  5. customThe residue was purified by column chromatography (silica, dichloromethane/methanol)

Sources & evidence

ORD record
ord-f1a296cd04a1414ea512c5e42f009ee4
Source dataset
uspto-grants-2015_12
Patent number
US09221843B2

Reaction notes

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