Hydrochloric Acid → HCID 24948150, compound

HRID 1667499Notes

Reaction equation

HRID 1667499 reaction equation
[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([NH:14][C:15]([C:17]3[CH:18]=[C:19]4[C:24](=[CH:25][CH:26]=3)[C:23](Cl)=[N:22][N:21]=[C:20]4[Cl:28])=[O:16])[CH:11]=[CH:12][CH:13]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+].[O:31]1CCOCC1.Cl>O>[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([NH:14][C:15]([C:17]3[CH:18]=[C:19]4[C:24](=[CH:25][CH:26]=3)[C:23](=[O:31])[NH:22][N:21]=[C:20]4[Cl:28])=[O:16])[CH:11]=[CH:12][CH:13]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 86620972HCID 86620972, compound

Product 1

HCID 24948150HCID 24948150, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 1,4-dichloro-phthalazine-6-carboxylic acid (3-piperidin-1-ylmethyl-phenyl)-amide (257 mg, 0.619 mmol), 2N NaOH (3.1 mL, 6.19 mmol) and dioxane (5 mL) was heated to 50° C. for 1 h. The reaction was diluted with water, acidified with conc. HCl to ˜pH 6. The reaction mixture was concentrated to low volume and filtered through celite. Preparatory HPLC afforded the desired regioisomer 4-chloro-1-oxo-1,2-dihydro-phthalazine-6-carboxylic acid (3-piperidin-1-ylmethyl-phenyl)-amide hydroformate (16 mg) as a pale yellow solid, 1H NMR (400 MHz, d6-DMSO) δ: 1.54 (m, 2H), 1.44 (m, 4H), 2.28 (m, 4H), 3.37 (s, 2H), 7.00 (m, 1H), 7.25 (m, 1H), 7.67 (m, 2H), 8.06 (d, 1H), 8.10 (s, 1H), 8.47 (dd, 1H), 8.82 (d, 1H), 10.63 (1H), 12.95 (s, 1H) ppm; m/z (M+1) 396.95.

Workup

  1. concentrationThe reaction mixture was concentrated to low volume
  2. filtrationfiltered through celite

Sources & evidence

ORD record
ord-fa8518d30c184cb98b323ac9dbc2fa29
Source dataset
uspto-grants-2011_10
Patent number
US08044041B2

Reaction notes

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