Trifluoroacetic acid → 4-[(3R,4S)-3-(4-Chloro-phenyl)-4-methylamino-pyrrolidine-1-carbonyl]-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-5'-carbonitrile

HRID 587368Notes

Reaction equation

HRID 587368 reaction equation
C(O[C:6](=O)[N:7]([C@H:9]1[C@H:13]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)[CH2:12][N:11]([C:21]([CH:23]2[CH2:28][CH2:27][N:26]([C:29]3[CH:34]=[CH:33][C:32]([C:35]#[N:36])=[CH:31][N:30]=3)[CH2:25][CH2:24]2)=[O:22])[CH2:10]1)C)(C)(C)C.FC(F)(F)C(O)=O>C(#N)C>[Cl:20][C:17]1[CH:18]=[CH:19][C:14]([C@H:13]2[C@H:9]([NH:7][CH3:6])[CH2:10][N:11]([C:21]([CH:23]3[CH2:24][CH2:25][N:26]([C:29]4[CH:34]=[CH:33][C:32]([C:35]#[N:36])=[CH:31][N:30]=4)[CH2:27][CH2:28]3)=[O:22])[CH2:12]2)=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58303011[(3S,4R)-4-(4-Chloro-phenyl)-1-(5'-cyano-3,4,5,6-tetrahydro-2H-[1,2]bipyridinyl-4-carbonyl)-pyrrolidin-3-yl]-methyl-carbamic acid tert-butyl ester

Product 1

HCID 672338234-[(3R,4S)-3-(4-Chloro-phenyl)-4-methylamino-pyrrolidine-1-carbonyl]-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-5'-carbonitrileYield 73.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of [(3S,4R)-4-(4-Chloro-phenyl)-1-(5′-cyano-3,4,5,6-tetrahydro-2H-[1,2]bipyridinyl-4-carbonyl)-pyrrolidin-3-yl]-methyl-carbamic acid tert-butyl ester (3.20 g, 6.12 mmol) in acetonitrile (30 mL) was added at ambient temperature trifluoroacetic acid (4.7 mL, 61.2 mmol) and the reaction mixture was stirred for 4 h at this temperature. After concentration, the residue was dissolved in ethyl acetate and washed with aqueous sodium carbonate (20%). The organic layer was dried over sodium sulfate and concentrated affording the title compound (1.90 g, 73%) as a light yellow foam. MS m/e: 424.2 [M+H]+.

Workup

  1. concentrationAfter concentration
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with aqueous sodium carbonate (20%)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c8c48ba2710e44c0bebc690219d61de6
Source dataset
uspto-grants-2016_01
Patent number
US09226916B2

Reaction notes

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