Hydrochloric Acid → HCID 57671688, compound

HRID 553520Notes

Reaction equation

HRID 553520 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[N:7][C:8]([C:12]#[C:13][Si](C)(C)C)=[CH:9][CH:10]=2)[N:5]([CH3:18])[C:4](=[O:19])[C:3]=1[C:20]([NH:22][CH2:23][C:24]([OH:26])=[O:25])=[O:21].C(=O)([O-])[O-].[K+].[K+].Cl>CO.C1COCC1>[C:12]([C:8]1[N:7]=[C:6]2[C:11]([C:2]([OH:1])=[C:3]([C:20]([NH:22][CH2:23][C:24]([OH:26])=[O:25])=[O:21])[C:4](=[O:19])[N:5]2[CH3:18])=[CH:10][CH:9]=1)#[CH:13]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 57671536HCID 57671536, compound

Product 1

HCID 57671688HCID 57671688, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
23 °C

Procedure

To a solution of 2-(4-hydroxy-1-methyl-2-oxo-7-(2-(trimethylsilyl)ethynyl)-1,2-dihydro-1,8-naphthyridine-3-carboxamido)acetic acid (183 mg, 490 μmol, Example 19 (b)) in MeOH (5 mL) and THF (5 mL) was added potassium carbonate (339 mg, 2450 mmol), and the reaction mixture was stirred at 23° C. for 23 hours. The mixture was acidified with concentrated HCl, and filtered. The filter cake was washed with water (10 mL), Et2O (10 mL) and DCM (10 mL), and dried in vacuo to give the title compound as a brown solid. MS (ESI, pos. ion) m/z: 302 (M+1). 1H NMR (400 MHz, DMSO-d6) δ ppm: 10.22-10.52 (m, 1 H), 8.43 (d, J=8.0 Hz, 1 H), 7.54 (d, J=8.2 Hz, 1 H), 4.74 (s, 1 H), 4.14 (d, J=5.5 Hz, 2 H), 3.64 (s, 3 H).

Workup

  1. filtrationfiltered
  2. washThe filter cake was washed with water (10 mL), Et2O (10 mL) and DCM (10 mL)
  3. customdried in vacuo

Sources & evidence

ORD record
ord-b165718afe564c75aef31c990d029201
Source dataset
uspto-grants-2011_11
Patent number
US08048892B2

Reaction notes

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