Hydrochloric Acid → HCID 22050916, compound

HRID 1866973Notes

Reaction equation

HRID 1866973 reaction equation
[Cl:1][C:2]1[C:3](=[O:35])[N:4]([C:18]2[C:32]([F:33])=[CH:31][C:21]([CH2:22][NH:23]C(=O)OC(C)(C)C)=[CH:20][C:19]=2[F:34])[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=1[F:17].Cl>O1CCCC1>[ClH:1].[NH2:23][CH2:22][C:21]1[CH:20]=[C:19]([F:34])[C:18]([N:4]2[CH:5]=[CH:6][C:7]([O:8][CH2:9][C:10]3[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=3[F:17])=[C:2]([Cl:1])[C:3]2=[O:35])=[C:32]([F:33])[CH:31]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22051020HCID 22051020, compound

Product 1

HCID 22050916HCID 22050916, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

tert-butyl 4-[3-chloro-4-[(2,4-difluorobenzyl)oxy]-2-oxopyridin-1(2H)-yl]-3,5-difluorobenzylcarbamate (from step 3) (1.39 g, 2.71 mmol) was dissolved in 20 ml tetrahydrofuran and treated with 4 ml concentrated hydrochloric acid. The solution was evaporated and dried in vacuo to a fine white solid (1.20 g, 99%). 1H-NMR (400 MHz, DMSO-d6) δ 8.54 (m, 2H), 7.86 (d, J=7.57 Hz, 1H), 7.65 (quartet, J=7.62, 1H), 7.50 (d, J=9.25 Hz, 2H), 7.34 (dt, J=10.50, 2.45 Hz, 1H), 7.16 (dt, J=8.38, 2.55 Hz, 1H), 6.78 (d, J=7.86 Hz, 1H), 5.37 (s, 2H), 4.10 (br s, 2H), 4.97-3.14 (v br s, 3H). 19F-NMR (400 MHz, DMSO-d6) δ −109.21 (quintet, J=7.77 Hz, 1F), −113.51 (quartet, J=8.95 Hz, 1F), −119.56 (d, J=9.44 Hz, 2F). LC/MS tr=4.33 minutes (0-95% acetonitrile/water, 0.05% trifluoroacetic acid, over 6 minutes at 1 ml/min with detection at 215 nm, at 50° C.) ES-MS m/z 413 (M+H). ES-HRMS m/z 413.0712 (M+H calcd for C19H14ClF4N2O2 requires 413.0674).

Workup

  1. customThe solution was evaporated
  2. dry with materialdried in vacuo to a fine white solid (1.20 g, 99%)
  3. customLC/MS tr=4.33 minutes (0-95% acetonitrile/water, 0.05% trifluoroacetic acid, over 6 minutes at 1 ml/min with detection at 215 nm, at 50° C.) ES-MS m/z 413 (M+H)

Sources & evidence

ORD record
ord-b26894ef495f46bfba9a4a2a586fd07c
Source dataset
uspto-grants-2009_12
Patent number
US07629363B2

Reaction notes

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