HCID 21912807, compound → HCID 21912738, compound

HRID 1245595Notes

Reaction equation

HRID 1245595 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[N:18]([CH2:19][CH3:20])[N:17]=[C:16]([CH3:21])[C:15]=2[O:22][CH3:23])[CH2:10][CH2:9]1)=O)(C)(C)C>FC(F)(F)C(O)=O.C(Cl)Cl>[CH2:19]([N:18]1[C:14]([CH:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)=[C:15]([O:22][CH3:23])[C:16]([CH3:21])=[N:17]1)[CH3:20]

Participants

4

Reactant 1

HCID 21912807HCID 21912807, compound

Product 1

HCID 21912738HCID 21912738, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 16 mg (0.0.49 mmol) of 1-tert-butoxycarbonyl-4-(1-ethyl-4-methoxy-3-methyl-(1H)-pyrazol-5-yl)piperidine (from Step E) in 0.1 mL of trifluoroacetic acid and 0.15 mL of CH2Cl2 at 0° C. was stirred for 30 min. Volatiles were removed under reduced pressure. The crude product was partitioned between 25 mL of 1 N NaOH and 25 mL of CH2Cl2. After separating phases, the aqueous layer was extracted with 3×25 mL of CH2Cl2. The combined organic layers were dried over Na2SO4 and concentrated to afford the title compound as a yellow film: 1H-NMR (500 MHz) δ 1.36 (t, J=7.2, 3H), 1.72–1.74 (m, 2H), 1.91–2.03 (m, 2H), 2.07 (s, 1H), 2.21 (s, 3H), 2.65–2.73 (m, 3H), 3.19–3.21 (m, 2H), 3.71 (s, 3H), 3.99 (q, J=7.2, 2H).

Workup

  1. customVolatiles were removed under reduced pressure
  2. customThe crude product was partitioned between 25 mL of 1 N NaOH and 25 mL of CH2Cl2
  3. customAfter separating phases
  4. extractionthe aqueous layer was extracted with 3×25 mL of CH2Cl2
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-7595a374cab646bdafacde4b6eab4075
Source dataset
uspto-grants-2006_10
Patent number
US07125887B2

Reaction notes

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