Hydrochloric Acid → HCID 18617528, compound

HRID 1264236Notes

Reaction equation

HRID 1264236 reaction equation
C[O:2][C:3](=[O:22])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13](=[O:16])[N:12]([CH2:17][CH2:18][N:19]([CH3:21])[CH3:20])[N:11]=2)=[CH:6][CH:5]=1.C1COCC1.CO.[OH-].[Na+].Cl>O>[CH3:20][N:19]([CH3:21])[CH2:18][CH2:17][N:12]1[C:13](=[O:16])[CH:14]=[CH:15][C:10]([C:7]2[CH:6]=[CH:5][C:4]([C:3]([OH:22])=[O:2])=[CH:9][CH:8]=2)=[N:11]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21899815MeOH tetrahydrofuranHCID 53922765HCID 53922765, compound

Product 1

HCID 18617528HCID 18617528, compoundYield 94.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 4-[1-(2-dimethylamino-ethyl)-6-oxo-1,6-dihydro-pyridazin-3-yl]-benzoic acid methyl ester (542 mg, 1.8 mmol, reference example 62a) in 1:1 THF/methanol (6 mL) is added 10N NaOH (1.8 mL, 18 mmol) followed by H2O (0.5 mL). The resulting solution is stirred for 1.5 hours then cooled to 0°-5° C., adjusted to pH 6 with 2N HCl and concentrated. The residue is purified by reverse phase HPLC (eluting with 15%-40% acetonitrile(0.1%TFA)/H2O(0.1%TFA) over 20 min) to give 487 mg of title compound. 1H NMR (DMSO) δ 2.89 (s, 6H), 3.59 (m, 2H), 4.52 (bt, 2H), 7.14 (d, J=10 Hz, 1H), 8.04 (s, 4H), 8.16 (d, J=10 Hz, 1H), 9.63 (bs, 1H). MS (ion spray) m/z 288 (M+H)+.

Workup

  1. temperaturethen cooled to 0°-5° C.
  2. concentrationconcentrated
  3. customThe residue is purified by reverse phase HPLC (eluting with 15%-40% acetonitrile(0.1%TFA)/H2O(0.1%TFA) over 20 min)

Sources & evidence

ORD record
ord-f5f13d8fa0e141e4b271b0334180056c
Source dataset
uspto-grants-2003_04
Patent number
US06541505B1

Reaction notes

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