Hydrochloric Acid → HCID 69062500, compound

HRID 227639Notes

Reaction equation

HRID 227639 reaction equation
[NH2:1][C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][C:18]([NH:20][C:21]4[CH:26]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:24]=[CH:23][C:22]=4[F:31])=[O:19])=[CH:13][C:12]=3[O:32]CC3C=CC=CC=3)=[CH:9][S:8][C:4]=2[N:5]=[CH:6][N:7]=1.O.[OH-].[Na+].Cl>Br.C(O)(=O)C.C(O)(=O)C>[NH2:1][C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][C:18]([NH:20][C:21]4[CH:26]=[C:25]([C:27]([F:30])([F:28])[F:29])[CH:24]=[CH:23][C:22]=4[F:31])=[O:19])=[CH:13][C:12]=3[OH:32])=[CH:9][S:8][C:4]=2[N:5]=[CH:6][N:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 69059651HCID 69059651, compound

Product 1

HCID 69062500HCID 69062500, compoundYield 19.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 21893785Acetic Acid Mixture with Hydrobromic AcidSolvent

Procedure

A solution of Example 351B (99 mg, 0.18 mmol) in 30% HBr/acetic acid (1 mL) and acetic acid (2 mL) was stirred at 70° C. for 3 hours, cooled to room temperature, poured into water, basified with 2N NaOH, adjusted to pH to 7-8 with 1N HCl, and extracted with methanol/dichloromethane. The extract was concentrated and the residue was purified by silica gel chromatography with 5% methanol/dichloromethane to provide 16 mg (19% yield) of the desired product. MS(ESI(+)) m/e 464.0 (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ 6.94 (dd, J=8.5, 2.0 Hz, 1H); 7.15 (d, J=8.1 Hz, 1H); 7.31 (s, 1H); 7.38-7.43 (m, 2H; 7.48-7.55 (m, 1H); 8.30 (s, 1H); 8.64 (dd, J=7.5, 2.4 Hz, 1H); 8.91 (d, J=2.7 Hz, 1H); 9.29 (s, 1H); 9.87 (s, 1H)

Workup

  1. extractionextracted with methanol/dichloromethane
  2. concentrationThe extract was concentrated
  3. customthe residue was purified by silica gel chromatography with 5% methanol/dichloromethane

Sources & evidence

ORD record
ord-65b39e376ff243e48f49f83a20ea4495
Source dataset
uspto-grants-2009_07
Patent number
US07560552B2

Reaction notes

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