Hydrochloric Acid → HCID 89601754, compound

HRID 869071Notes

Reaction equation

HRID 869071 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([N:10]2[CH:17]([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=3[CH3:25])[C:16]3[C:12](=[N:13][N:14]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=4[O:35][CH3:36])[C:15]=3[CH:26]([CH3:28])[CH3:27])[C:11]2=[O:37])[CH:9]=1)[C:5]#[N:6].Cl.[OH2:39]>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([N:10]2[CH:17]([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=3[CH3:25])[C:16]3[C:12](=[N:13][N:14]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=4[O:35][CH3:36])[C:15]=3[CH:26]([CH3:28])[CH3:27])[C:11]2=[O:37])[CH:9]=1)[C:5]([NH2:6])=[O:39]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 89602056HCID 89602056, compound

Product 1

HCID 89601754HCID 89601754, compound

Conditions

Temperature
70 °C

Procedure

A mixture of the compound prepared in example 103 (100 mg, 0.188 mmol) and concentrated HCl (10 mL) was heated to 70° C. and stirred at this temperature overnight. The reaction mixture was allowed to cool to rt, diluted with water and extracted with EtOAc. The organic layer was washed with a saturated aqueous solution of sodium bicarbonate and water, dried (Na2SO4), filtered, and concentrated. The residue was purified by silica gel column chromatography (CHCl3/MeOH, 99:1) to afford the title compound. tR: 6.02 min (HPLC 2); ESI-MS: 549 [M+H]+ (LC-MS 2); Rf=0.47 (CHCl3/MeOH, 9:1).

Workup

  1. temperatureto cool to rt
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with a saturated aqueous solution of sodium bicarbonate and water
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography (CHCl3/MeOH, 99:1)

Sources & evidence

ORD record
ord-38ee9d73127741ed9865c913e0ed3fa1
Source dataset
uspto-grants-2015_03
Patent number
US08969341B2

Reaction notes

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