Trifluoroacetic acid → (3-(Methoxymethyl)pyrrolidin-3-yl)(3-(trifluoromethyl)-7,8-dihydro-1,6-naphthyridin-6(5H)-yl)methanone 2,2,2-trifluoroacetate

HRID 1045359Notes

Reaction equation

HRID 1045359 reaction equation
[CH3:1][O:2][CH2:3][C:4]1([C:16]([N:18]2[CH2:27][CH2:26][C:25]3[N:24]=[CH:23][C:22]([C:28]([F:31])([F:30])[F:29])=[CH:21][C:20]=3[CH2:19]2)=[O:17])[CH2:8][CH2:7][N:6](C(OC(C)(C)C)=O)[CH2:5]1.[C:32]([OH:38])([C:34]([F:37])([F:36])[F:35])=[O:33]>C(Cl)Cl>[F:35][C:34]([F:37])([F:36])[C:32]([OH:38])=[O:33].[CH3:1][O:2][CH2:3][C:4]1([C:16]([N:18]2[CH2:27][CH2:26][C:25]3[N:24]=[CH:23][C:22]([C:28]([F:30])([F:29])[F:31])=[CH:21][C:20]=3[CH2:19]2)=[O:17])[CH2:8][CH2:7][NH:6][CH2:5]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59569553tert-Butyl 3-(methoxymethyl)-3-(3-(trifluoromethyl)-5,6,7,8-tetrahydro-1,6-naphthyridine-6-carbonyl)pyrrolidine-1-carboxylate

Product 1

HCID 86647285(3-(Methoxymethyl)pyrrolidin-3-yl)(3-(trifluoromethyl)-7,8-dihydro-1,6-naphthyridin-6(5H)-yl)methanone 2,2,2-trifluoroacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared according to general procedure D described in connection with Scheme 2. tert-Butyl 3-(methoxymethyl)-3-(3-(trifluoromethyl)-5,6,7,8-tetrahydro-1,6-naphthyridine-6-carbonyl)pyrrolidine-1-carboxylate (1.7 g, 3.84 mmole) was dissolved in 50 mL CH2Cl2 and 16 mL TFA was added at RT. The reaction mixture was stirred for 17 h and the solvents evaporated. The residue was dissolved in CH2Cl2 and the organic layer was washed twice with 50 mL of saturated NaHCO3 and then dried over Na2SO4. The solvent was evaporated to give product (1.3 g, quantitative yield) of the desired product. 1H NMR (400 MHz, CDCl3): δ 8.71 (s, 1H), 7.70 (s, 1H), 4.81 (s, 2H), 4.13-3.89 (m, 2H), 3.52-3.43 (m, 3H), 3.29 (s, 3H), 3.12-2.97 (m, 5H), 2.22-2.18 (m, 1H), 2.04-1.97 (m, 1H); MS (ESI) m/z: Calculated for C16H20F3N3O2(free base): 343.2. found: 344 (M+H)+.

Workup

  1. customThe title compound was prepared
  2. customthe solvents evaporated
  3. dissolutionThe residue was dissolved in CH2Cl2
  4. washthe organic layer was washed twice with 50 mL of saturated NaHCO3
  5. dry with materialdried over Na2SO4
  6. customThe solvent was evaporated

Sources & evidence

ORD record
ord-351532d60ab04080bc952480abe36233
Source dataset
uspto-grants-2013_10
Patent number
US08569282B2

Reaction notes

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