Hydrochloric Acid → HCID 58019983, compound

HRID 1632093Notes

Reaction equation

HRID 1632093 reaction equation
[CH3:1][O:2][C:3]1[C:8]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=2)=[CH:7][C:6]([CH2:18][N:19]2[CH:24]=[CH:23][C:22]([C:25]#[N:26])=[CH:21][C:20]2=[O:27])=[CH:5][CH:4]=1.Cl.[OH-:29].[Na+]>>[CH3:1][O:2][C:3]1[C:8]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=2)=[CH:7][C:6]([CH2:18][N:19]2[CH:24]=[CH:23][C:22]([C:25]([NH2:26])=[O:29])=[CH:21][C:20]2=[O:27])=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 57703744HCID 57703744, compound

Product 1

HCID 58019983HCID 58019983, compoundYield 22%

Procedure

Into a 20 mL vial with a stir bar was added P-196 (132 mg, 0.37 mmol) and concentrated HCl (2 mL). The reaction was stirred at rt for 18 hours, basified with 4N aqueous NaOH, and the product was extracted with ethyl acetate (3×5 mL). The combined organics were concentrated to half their original volume and 5 mL of hexane was added. The resulting solids were filtered, washed with hexane, and triturated with ether to afford 29.8 mg (22%) of P-207 as a tan solid. 1H NMR (400 MHz, DMSO-d6) 8.28 (s, 1H), 8.20 (dd, J=1.4, 8.3 Hz, 1H), 8.05 (br. s., 1H), 7.93 (t, J=7.4 Hz, 2H), 7.72 (t, J=8.0 Hz, 1H), 7.61 (br s, 1H), 7.48 (d, J=2.0 Hz, 1H), 7.42 (dd, J=2.1, 8.5 Hz, 1H), 7.15 (d, J=8.5 Hz, 1H), 6.84 (d, J=1.5 Hz, 1H), 6.54 (dd, J=1.8, 7.0 Hz, 1H), 5.10 (s, 2H), 3.79 (s, 3H) ppm. MS: 380.1 (APCI+).

Workup

  1. extractionthe product was extracted with ethyl acetate (3×5 mL)
  2. concentrationThe combined organics were concentrated to half their original volume and 5 mL of hexane
  3. additionwas added
  4. filtrationThe resulting solids were filtered
  5. washwashed with hexane
  6. customtriturated with ether

Sources & evidence

ORD record
ord-b292e48c547b4d04ad4b5db864ee417a
Source dataset
uspto-grants-2014_07
Patent number
US08791267B2

Reaction notes

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