Hydrochloric Acid → HCID 25111160, compound

HRID 1009746Notes

Reaction equation

HRID 1009746 reaction equation
[CH2:1]([N:3]1[CH:7]=[C:6]([NH:8][C:9](=[O:34])[CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][C:18]3[C:27]4[C:22](=[CH:23][C:24]([O:32][CH3:33])=[C:25]([C:28]([O:30]C)=[O:29])[CH:26]=4)[N:21]=[CH:20][CH:19]=3)=[CH:13][CH:12]=2)[CH:5]=[N:4]1)[CH3:2].[OH-].[Li+].Cl>CO>[CH2:1]([N:3]1[CH:7]=[C:6]([NH:8][C:9](=[O:34])[CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][C:18]3[C:27]4[C:22](=[CH:23][C:24]([O:32][CH3:33])=[C:25]([C:28]([OH:30])=[O:29])[CH:26]=4)[N:21]=[CH:20][CH:19]=3)=[CH:13][CH:12]=2)[CH:5]=[N:4]1)[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 25112108Methyl 4-[4-[2-[(1-ethyl-1H-pyrazol-4-yl)amino]-2-oxoethyl]phenoxy]-7-methoxy-6-quinolinecarboxylate

Product 1

HCID 25111160HCID 25111160, compoundYield 57.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of N-(1-ethylpyrazol-4-yl)-2-[4-(7-methoxy-6-methoxycarbonylquinolin-4-yloxy)phenyl]acetamide (0.05 g), lithium hydroxide (0.01 g) and methanol (1 ml) was stirred at ambient temperature for 14 hours. The resultant mixture was acidified to pH2 by the addition of 2N aqueous hydrochloric acid. The precipitate was isolated, washed with water and with diethyl ether and dried under vacuum. There was thus obtained the title compound (0.028 g); 1H NMR: (DMSOd6) 1.32 (t, 3H), 3.63 (s, 2H), 3.97 (s, 3H), 4.03-4.11 (m, 2H), 6.48 (d, 1H), 7.27 (d, 2H), 7.42 (s, 1H), 7.46 (d, 2H), 7.5 (s, 1H), 7.9 (s, 1H), 8.54 (s, 1H), 6.67 (d, 1H), 10.21 (s, 1H); Mass Spectrum: M+H+ 447.

Workup

  1. customThe precipitate was isolated
  2. washwashed with water and with diethyl ether
  3. customdried under vacuum

Sources & evidence

ORD record
ord-b7a84ee4b7454b7a86c402f4ee2c9ecb
Source dataset
uspto-grants-2011_07
Patent number
US07973164B2

Reaction notes

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