Hydrochloric Acid → HCID 22050202, compound

HRID 1867184Notes

Reaction equation

HRID 1867184 reaction equation
[Br:1][C:2]1[C:3](=[O:34])[N:4]([C:19]2[CH:20]=[C:21]([NH:26]C(=O)OC(C)(C)C)[CH:22]=[CH:23][C:24]=2[F:25])[C:5]([CH3:18])=[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].[ClH:35]>O1CCCC1>[ClH:35].[NH2:26][C:21]1[CH:22]=[CH:23][C:24]([F:25])=[C:19]([N:4]2[C:5]([CH3:18])=[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]([Br:1])[C:3]2=[O:34])[CH:20]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22050673HCID 22050673, compound

Product 1

HCID 22050202HCID 22050202, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The product of Step 1, (2.9 g, 5.3 mmol) was dissolved in tetrahydrofuran (75 mL) and 6N HCl (10 mL). The reaction mixture was heated at 60 C for 18 h and was concentrated in vacuo to give the final product (1.89 g, 75%). 1H NMR (400 MHz, CD3OD) δ 7.64 (q, J=8.4 and 15.2 Hz, 1H), 7.56 (m, 2H), 7.46 (m, 1H), 7.05 (m, 2H), 6.69 (s, 1H), 5.37 (s, 2H), 2.10 (s, 3H) ppm. 19F NMR (400 MHz, CD3OD) δ −111.37 (1F), −115.86 (1F), −123.16 ppm. ES-HRMS m/z 440.0334 (M+H calcd for C19H15BrF3N2O2 requires 440.0295).

Workup

  1. temperatureThe reaction mixture was heated at 60 C for 18 h
  2. concentrationwas concentrated in vacuo

Sources & evidence

ORD record
ord-1d583f8da6824feca0883b7cda479b92
Source dataset
uspto-grants-2009_12
Patent number
US07629363B2

Reaction notes

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