Lithium hydroxide, monohydrate → HCID 58864188, compound

HRID 1353454Notes

Reaction equation

HRID 1353454 reaction equation
C([O:3][C:4](=[O:27])[CH2:5][NH:6][C:7]([N:9]1[CH2:14][CH2:13][N:12]([C:15]2[C:24]3[C:19](=[CH:20][C:21]([Cl:25])=[CH:22][CH:23]=3)[N:18]=[C:17]([NH2:26])[CH:16]=2)[CH2:11][CH2:10]1)=[O:8])C.O[Li].O>C1COCC1.O>[NH2:26][C:17]1[CH:16]=[C:15]([N:12]2[CH2:13][CH2:14][N:9]([C:7]([NH:6][CH2:5][C:4]([OH:27])=[O:3])=[O:8])[CH2:10][CH2:11]2)[C:24]2[C:19](=[CH:20][C:21]([Cl:25])=[CH:22][CH:23]=2)[N:18]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 69515578HCID 69515578, compound

Product 1

HCID 58864188HCID 58864188, compoundYield 82.7%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

As described example 159, 7-chloro-4-(1-piperazinyl)-2-quinolinamine (1.5 g, 5.7 mmol), isocyanato-acetic acid-ethy ester (0.7 mL, 6.3 mmol) and diisopropylethyl amine (1.5 mL, 8.6 mmol) are reacted to give [[[4-(2-amino-7-chloro-4-quinolinyl)-1-piperazinyl]carbonyl]amino]-acetic acid-ethyl ester the product as a white solid (990 mg, 40%). A mixture of the ester (990 mg), LiOH.H2O (1 g) in THF-H2O (5:1, 45 mL) was stirred at rt for 3 h, then acidified with 1.0 N HC (aq.) to pH to 4–5. After the removal of THF in vacuo, crude product precipitated. 760 mg (76%) of the acid was obtained after drying under vacuum for 3 h. LC-MS: 363 (M++1).

Workup

  1. customAfter the removal of THF in vacuo, crude product
  2. customprecipitated

Sources & evidence

ORD record
ord-1041621530234042a1fb8c829180f0f0
Source dataset
uspto-grants-2007_05
Patent number
US07220856B2

Reaction notes

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