Hydrochloric Acid → HCID 22142171, compound

HRID 2414506Notes

Reaction equation

HRID 2414506 reaction equation
C[O:2][C:3]([C:5]1[CH:14]=[C:13]([O:15]COCC[Si](C)(C)C)[C:12]2[C:7](=[C:8]([N:26]3[CH2:32][CH2:31][CH2:30][N:29]([CH3:33])[CH2:28][CH2:27]3)[CH:9]=[C:10]([O:24][CH3:25])[CH:11]=2)[N:6]=1)=[O:4].O1CCCC1.O.[OH-].[Li+].Cl>O.CO>[CH3:25][O:24][C:10]1[CH:11]=[C:12]2[C:7](=[C:8]([N:26]3[CH2:32][CH2:31][CH2:30][N:29]([CH3:33])[CH2:28][CH2:27]3)[CH:9]=1)[NH:6][C:5]([C:3]([OH:4])=[O:2])=[CH:14][C:13]2=[O:15]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 69269583HCID 69269583, compound

Product 1

HCID 22142171HCID 22142171, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a light brown solution of 6-methoxy-8-(4-methyl-[1,4]diazepan-1-yl)-4-(2-trimethylsilanyl-ethoxymethoxy)-quinoline-2-carboxylic acid methyl ester (1.00 g, 2.10 mmol) in 18 mL 3:1:1 tetrahydrofuran:methanol:water was added lithium hydroxide monohydrate (0.267 g, 6.35 mmol). The reaction mixture was stirred at room temperature for 5 hours, acidified to pH 4 with 1 N HCl, and stirred an additional 20 minutes. The reaction mixture was concentrated and dried under high vacuum to afford an orange foam. 1H NMR (300 MHz, DMSO, d6) δ 11.06 (s, 1H, NH), 7.53 (s, 1H, C═CH), 7.00 (d, 1H, Jm=2.4 Hz, ArH5), 6.70 (d, 1H, Jm=2.4 Hz, ArH7), 4.05-3.99 (m, 2H, ArNCH2CH2CH2NCH3), 3.87 (s, 3H, OCH3), 3.68-3.60 (m, 2H, ArNCH2CH2NCH3), 3.54-3.47 (m, 2H, ArNCH2CH2NCH3), 3.41-3.26 (m, 2H, ArNCH2CH2CH2NCH3), 2.82 (d, 3H, J=4.8 Hz, NCH3), 2.46-2.41 (m, 1H, ArNCH2CH2CH2NCH3), 2.30-2.25 (m, 1H, ArNCH2CH2CH2NCH3); Mass Spec.: calc. for [C17H21N3O4+H]+ Theor. m/z 332; Obs. 332.

Workup

  1. stirringstirred an additional 20 minutes
  2. concentrationThe reaction mixture was concentrated
  3. customdried under high vacuum
  4. customto afford an orange foam

Sources & evidence

ORD record
ord-ff82b084c00844188893deda6dd3c63c
Source dataset
uspto-grants-2004_11
Patent number
US06812225B2

Reaction notes

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