Trifluoroacetic acid → [5-Cyclopropyl-6-(4-fluoro-benzyl)-pyridin-2-yl]-(1,8-diaza-spiro[4.5]dec-1-yl)-methanone

HRID 624973Notes

Reaction equation

HRID 624973 reaction equation
C(OC([N:8]1[CH2:36][CH2:35][C:11]2([N:15]([C:16]([C:18]3[CH:23]=[CH:22][C:21]([CH:24]4[CH2:26][CH2:25]4)=[C:20]([CH2:27][C:28]4[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=4)[N:19]=3)=[O:17])[CH2:14][CH2:13][CH2:12]2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH:24]1([C:21]2[CH:22]=[CH:23][C:18]([C:16]([N:15]3[C:11]4([CH2:35][CH2:36][NH:8][CH2:9][CH2:10]4)[CH2:12][CH2:13][CH2:14]3)=[O:17])=[N:19][C:20]=2[CH2:27][C:28]2[CH:29]=[CH:30][C:31]([F:34])=[CH:32][CH:33]=2)[CH2:26][CH2:25]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 902035641-[5-Cyclopropyl-6-(4-fluoro-benzyl)-pyridine-2-carbonyl]-1,8-diaza-spiro[4.5]decane-8-carboxylic acid tert-butyl ester

Product 1

HCID 76281070[5-Cyclopropyl-6-(4-fluoro-benzyl)-pyridin-2-yl]-(1,8-diaza-spiro[4.5]dec-1-yl)-methanoneYield 92.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl 1-(5-cyclopropyl-6-(4-fluorobenzyl)picolinoyl)-1,8-diazaspiro[4.5]decane-8-carboxylate (Example 111, 19 mg, 38.5 μmol) and 2,2,2-trifluoroacetic acid (43.9 mg, 29.5 μL, 385 μmol) in DCM (0.4 mL) was stirred for 12 h at ambient temperature. The reaction mixture was poured onto 20 mL saturated aqueous NaHCO3 solution/ice and extracted with EtOAc (2×20 mL). The combined extracts were washed with ice-water/brine (20 mL), dried over Na2SO4 and brought to dryness to give the title compound (14 mg, 92%) as colorless oil; MS (EI): m/e=394.5 [MH+].

Workup

  1. extractionextracted with EtOAc (2×20 mL)
  2. washThe combined extracts were washed with ice-water/brine (20 mL)
  3. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-35ee1ec2ca494a57a2d710ec0372f11d
Source dataset
uspto-grants-2016_04
Patent number
US09303012B2

Reaction notes

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