Trifluoroacetic acid → HCID 59375596, compound

HRID 2192986Notes

Reaction equation

HRID 2192986 reaction equation
[CH:1]1([C:4]#[C:5][C:6]2[C:15]3[N:14]=[C:13]([NH:16][C@H:17]4[CH2:22][CH2:21][CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18]4)[C:12]4[CH:30]=[CH:31][N:32]=[CH:33][C:11]=4[C:10]=3[C:9](=[O:34])[NH:8][CH:7]=2)[CH2:3][CH2:2]1.FC(F)(F)C(O)=O>ClCCl>[CH:1]1([C:4]#[C:5][C:6]2[C:15]3[N:14]=[C:13]([NH:16][C@H:17]4[CH2:22][CH2:21][CH2:20][NH:19][CH2:18]4)[C:12]4[CH:30]=[CH:31][N:32]=[CH:33][C:11]=4[C:10]=3[C:9](=[O:34])[NH:8][CH:7]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59375468HCID 59375468, compound

Product 1

HCID 59375596HCID 59375596, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl (3S)-3-{[4-(cyclopropylethynyl)-1-oxo-1,2-dihydropyrido[4,3-c]-1,6-naphthyridin-6-yl]amino}piperidine-1-carboxylate (100 mg, 0.218 mmol) in dichloromethane (2 mL), trifluoroacetic acid (2000 26.0 mmol) was added. After stirring at room temperature for 10 min, the mixture was quenched with aqueous sodium hydrogen carbonate (saturated). The aqueous layer was extracted with ethyl acetate. The combined organic extracts were dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by preparative HPLC Reverse phase (C-18), eluting with Acetonitrile/Water+0.05% TFA, to afford 4-(cyclopropylethynyl)-6-[(3S)-piperidin-3-ylamino]pyrido[4,3-c]-1,6-naphthyridin-1(2H)-one as a yellow solid. 1H NMR (500 MHz, C2D6SO) δ 10.97 (s, 1H), 8.74 (d, 1H), 8.29 (d, 1H), 8.06 (d, 1H), 7.61 (s, 1H), 4.42 (m, 1H), 3.03 (m, 2H), 2.74 (m, 1H), 2.16 (t, 2H), 1.66 (m, 2H), 0.84 (m, 6H). LRMS (APCI) calc'd for (C21H22N5O) [M+H]+, 360.2; found 360.1.

Workup

  1. customthe mixture was quenched with aqueous sodium hydrogen carbonate (saturated)
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. dry with materialThe combined organic extracts were dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by preparative HPLC Reverse phase (C-18)
  6. washeluting with Acetonitrile/Water+0.05% TFA

Sources & evidence

ORD record
ord-38f482a7171340aea01c1f0fc863a0e8
Source dataset
uspto-grants-2012_12
Patent number
US08329722B2

Reaction notes

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