Hydrochloric Acid → HCID 59736845, compound

HRID 252819Notes

Reaction equation

HRID 252819 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([O:16]C)=[O:15])=[CH:10][CH:9]=2)=[CH:4][C:3]=1[NH:18][C:19](=[O:28])[C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1.[OH-].[Na+].Cl>C1COCC1.O>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]([C:14]([OH:16])=[O:15])=[CH:12][CH:13]=2)=[CH:4][C:3]=1[NH:18][C:19](=[O:28])[C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59736856HCID 59736856, compound

Product 1

HCID 59736845HCID 59736845, compoundYield 80.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 104 (44 mg, 0.117) and NaOH 1M (0.24 ml, 0.24 mmol) in THF (1 ml) and water (1 ml) was stirred 48 h at 40° C. HCl 1M was added and the precipitate was filtered out. The solid was further purified by flash chromatography (eluent 3-5% MeOH in DCM), to give the compound 105 (34 mg, 80% yield). 1H NMR: (DMSO) δ (ppm): 9.61 (s, 1H), 7.98 (d, J=8.6 Hz, 2H), 7.93 (d, J=8.2 Hz, 2H), 7.66 (d, J=8.2 Hz, 2H), 7.58 (d, J=2.0 Hz, 1H), 7.40 (dd, J=8.2, 2.0 Hz, 1H), 7.04 (d, J=8.8 Hz, 2H), 6.86 (d, J=8.4 Hz, 1H), 5.23 (s, 2H), 3.84 (s, 3H). MS: (calc.) 362.1; (obt.) 363.1 (MH)+.

Workup

  1. filtrationthe precipitate was filtered out
  2. customThe solid was further purified by flash chromatography (eluent 3-5% MeOH in DCM)

Sources & evidence

ORD record
ord-089ff54ca2b04559995131c696bfe5f8
Source dataset
uspto-grants-2011_01
Patent number
US07868205B2

Reaction notes

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