Hydrochloric Acid → HCID 24801219, compound

HRID 386465Notes

Reaction equation

HRID 386465 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][C:23]([C:25]4[O:26][C:27]([C:30]5[N:35]=[C:34]([C:36]([O:38]C)=[O:37])[CH:33]=[CH:32][CH:31]=5)=[CH:28][N:29]=4)=[O:24])=[CH:17][CH:16]=3)=[CH:11][CH:10]=2)[CH2:4][CH2:3]1.[Li+].[OH-].Cl>C1COCC1.O.C(Cl)Cl>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([CH2:8][C:9]2[CH:10]=[CH:11][C:12]([C:15]3[CH:16]=[CH:17][C:18]([CH2:21][CH2:22][C:23]([C:25]4[O:26][C:27]([C:30]5[N:35]=[C:34]([C:36]([OH:38])=[O:37])[CH:33]=[CH:32][CH:31]=5)=[CH:28][N:29]=4)=[O:24])=[CH:19][CH:20]=3)=[CH:13][CH:14]=2)[CH2:6][CH2:7]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 25118518HCID 25118518, compound

Product 1

HCID 24801219HCID 24801219, compoundYield 21%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

Methyl 6-(2-(3-(4′-((4-methylpiperazin-1-yl)methyl)biphenyl-4-yl)propanoyl)oxazol-5-yl)pyridine-2-carboxylate (10 mg, 0.019 mmol) was dissolved in THF/H2O (3:2, 2 mL) and LiOH (1 mg, 0.06 mmol) was added. The reaction solution was stirred at room temperature under an atmosphere of Ar for 40 min before the addition of aqueous 1 N HCl to pH 4. The reaction solution was diluted with CH2Cl2 and the organic and aqueous layers were separated. The aqueous layer was made basic to pH 8 with the addition of saturated aqueous NaHCO3 and extracted with CH2Cl2. The organic phases were combined, dried over Na2SO4, and concentrated in vacuo. The crude product was purified by tritration in ether to provide 6-(2-(3-(4′-((4-methylpiperazin-1-yl)methyl)biphenyl-4-yl)propanoyl)oxazol-5-yl)pyridine-2-carboxylic acid as a white solid (2 mg, 21%): 1H NMR (CDCl3, 600 MHz) δ 8.17 (s, 1H), 7.93 (s, 3H), 7.48 (d, 2H, J=7.8 Hz), 7.44 (d, 2H, J=7.8 Hz), 7.31-7.27 (m, 4H), 3.68 (s, 2H), 3.47 (t, 2H, J=6.9 Hz), 3.15 (t, 2H, J=6.9 Hz), 2.82 (bs, 4H), 2.69 (s, 3H), 2.10-2.00 (m, 4H); HR ESI-TOF m/z 511.2334 (M+H+, C30H30N4O4, requires 511.2340).

Workup

  1. customthe organic and aqueous layers were separated
  2. additionThe aqueous layer was made basic to pH 8 with the addition of saturated aqueous NaHCO3
  3. extractionextracted with CH2Cl2
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by tritration in ether

Sources & evidence

ORD record
ord-ec4558a15a244c759856ce3fefee8397
Source dataset
uspto-grants-2013_02
Patent number
US08372823B2

Reaction notes

Loading…