Hydrochloric Acid → HCID 59469139, compound

HRID 1672933Notes

Reaction equation

HRID 1672933 reaction equation
[F:1][C:2]1[C:3]([NH:27][C:28]2[CH:33]=[CH:32][C:31]([I:34])=[CH:30][C:29]=2[F:35])=[C:4]([C:9]([N:11]2[CH2:14][C:13]([CH2:16][N:17]([CH2:25][CH3:26])C(=O)OC(C)(C)C)([F:15])[CH2:12]2)=[O:10])[CH:5]=[CH:6][C:7]=1[F:8].Cl>C(#N)C.O1CCOCC1>[CH2:25]([NH:17][CH2:16][C:13]1([F:15])[CH2:14][N:11]([C:9]([C:4]2[C:3]([NH:27][C:28]3[CH:33]=[CH:32][C:31]([I:34])=[CH:30][C:29]=3[F:35])=[C:2]([F:1])[C:7]([F:8])=[CH:6][CH:5]=2)=[O:10])[CH2:12]1)[CH3:26]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86621267HCID 86621267, compound

Product 1

HCID 59469139HCID 59469139, compoundYield 27.3%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 312751,4-DioxaneSolvent

Procedure

To the 1,1-dimethylethyl [{1-({3,4-difluoro-2-[(2-fluoro-4-iodophenyl)amino]phenyl}carbonyl)-3-fluoroazetidin-3-yl]methyl}ethylcarbamate (19.0 mg, 0.031 mmol) in acetonitrile (1.0 mL) added a solution 4.0N hydrogen chloride in dioxane (1.0 mL). After 1.5 hr the solution was concentrated in vacuo. The residue was purified by preparative reverse phase HPLC to afford the title compound (4.30 mg, 27%). 1H NMR (400 MHz, CDCl3): 8.25 (s, 1H), 7.33 (dd, 1H), 7.33-7.25 (m, 1H), 7.18-7.14 (m, 1H), 6.84-6.77 (m, 1H), 6.63-6.58 (m, 1H), 4.33-4.05 (br m, 4H), 3.07-2.95 (br m, 2H), 2.65 (q, 2H), 1.08 (t, 3H); MS (EI) for C19H18F4IN3O: 508 (MH+).

Workup

  1. concentrationAfter 1.5 hr the solution was concentrated in vacuo
  2. customThe residue was purified by preparative reverse phase HPLC

Sources & evidence

ORD record
ord-9c15fb65f49d4674895939dd122b9931
Source dataset
uspto-grants-2011_08
Patent number
US07999006B2

Reaction notes

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