Hydrochloric Acid → HCID 59132700, compound

HRID 1160290Notes

Reaction equation

HRID 1160290 reaction equation
[OH-].[K+].C([O:5][C:6](=[O:32])[CH2:7][CH:8]([C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20]2[C:24]([CH3:25])=[N:23][N:22]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[N:21]=2)=[CH:14][CH:13]=1)[C:9]#[C:10][CH3:11])C.O.Cl>CCO>[CH3:25][C:24]1[C:20]([CH2:19][O:18][C:15]2[CH:14]=[CH:13][C:12]([CH:8]([C:9]#[C:10][CH3:11])[CH2:7][C:6]([OH:32])=[O:5])=[CH:17][CH:16]=2)=[N:21][N:22]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[N:23]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14797Potassium HydroxideHCID 59132687HCID 59132687, compound

Product 1

HCID 59132700HCID 59132700, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2N KOH(aq) (1 mL) was added to a solution of 26.2 (68 mg, 0.17 mmol) in EtOH (2 mL). The reaction was stirred at room temperature overnight and then poured into water. The aqueous mixture was acidified to pH=2 with 1N HCl(aq), and then extracted with ethyl acetate. The organic layer was washed with water, followed by brine. The organic layer was then concentrated under reduced pressure and the resulting residue was purified via radial chromatography (20% ethyl acetate in hexanes) to yield 60.3 mg (95%) of compound 26 as a colorless oil. LC/MSD m/e: 374.0 (M−H); 1H NMR (400 MHz) (acetone-d6) δ 8.05 (2H, d, J=8.0 Hz), 7.56 (2H, t, J=8.0 Hz), 7.40 (3H, t, J=8.0 Hz), 7.06 (2H, d, J=8.0 Hz), 5.28 (2H, s), 4.05 (1H, m), 2.70 (2H, m), 2.44 (3H, s), 1.80 (3H, s).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. concentrationThe organic layer was then concentrated under reduced pressure
  4. customthe resulting residue was purified via radial chromatography (20% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-24bb9dcb375b42c58d0691bf42a27acd
Source dataset
uspto-grants-2010_10
Patent number
US07816367B2

Reaction notes

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