Hydrochloric Acid → HCID 86706869, compound

HRID 717889Notes

Reaction equation

HRID 717889 reaction equation
Cl.[OH:2][CH2:3][C:4]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[N:7]=[C:6]([NH:14][CH:15]2[CH2:20][CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17][CH2:16]2)[CH:5]=1.[OH-].[Na+]>O1CCOCC1>[NH:18]1[CH2:19][CH2:20][CH:15]([NH:14][C:6]2[CH:5]=[C:4]([CH2:3][OH:2])[CH:9]=[C:8]([C:10]([F:12])([F:11])[F:13])[N:7]=2)[CH2:16][CH2:17]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86706868HCID 86706868, compound

Product 1

HCID 86706869HCID 86706869, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

4.0 M Hydrogen chloride in dioxane (36 mL, 140 mmol) was added to a solution of tert-butyl 4-{[4-(hydroxymethyl)-6-(trifluoromethyl)pyridin-2-yl]amino}piperidine-1-carboxylate (2.7 g, 7.2 mmol, from Step 3) in 1,4-dioxane (18 mL). After stirring for 30 minutes, the mixture was then basified to pH 12-13 by the addition of 1.0 N NaOH. The product was extracted with DCM (6×). The combined organic extracts were dried over sodium sulfate, filtered and concentrated to afford the product as a white powder (1.64 g, 83%). 1H NMR (400 MHz, d6-DMSO) δ 6.94 (d, J=7.6 Hz, 1H), 6.77 (s, 1H), 6.67 (s, 1H), 5.39 (t, J=5.8 Hz, 1H), 4.42 (d, J=5.5 Hz, 2H), 3.76-3.60 (m, 1H), 2.92 (dt, J=12.4, 3.3 Hz, 2H), 2.57-2.43 (m, 2H), 1.87-1.77 (m, 2H), 1.25 (qd, J=11.8, 3.8 Hz, 2H). 19F NMR (376 MHz, d6-DMSO) δ −67.68 (s).

Workup

  1. extractionThe product was extracted with DCM (6×)
  2. dry with materialThe combined organic extracts were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-5348b3efa73e40649686b02d60c5d615
Source dataset
uspto-grants-2015_11
Patent number
US09193733B2

Reaction notes

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