Acetonitrile → HCID 131729016, compound

HRID 1011233Notes

Reaction equation

HRID 1011233 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([O:21][CH3:22])[C:11]=1[N:12]1[CH2:17][CH2:16][CH:15]([C:18]([OH:20])=[O:19])[CH2:14][CH2:13]1)[N:8]([CH2:23][C:24]([F:27])([F:26])[F:25])[CH:7]=[C:6]([C:28]([NH:30][CH2:31][C:32]1[CH:37]=[CH:36][C:35]([O:38][C:39]([F:42])([F:41])[F:40])=[CH:34][C:33]=1[CH3:43])=[O:29])[C:5]2=[O:44].C(#N)C.[OH-].[OH:49][CH2:50][CH2:51][N+:52]([CH3:55])([CH3:54])[CH3:53]>O>[OH:49][CH2:50][CH2:51][N+:52]([CH3:55])([CH3:54])[CH3:53].[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([O:21][CH3:22])[C:11]=1[N:12]1[CH2:17][CH2:16][CH:15]([C:18]([O-:20])=[O:19])[CH2:14][CH2:13]1)[N:8]([CH2:23][C:24]([F:27])([F:25])[F:26])[CH:7]=[C:6]([C:28]([NH:30][CH2:31][C:32]1[CH:37]=[CH:36][C:35]([O:38][C:39]([F:40])([F:41])[F:42])=[CH:34][C:33]=1[CH3:43])=[O:29])[C:5]2=[O:44]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 31255Choline, hydroxideHCID 57781000HCID 57781000, compound

Product 1

HCID 131729016HCID 131729016, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

400 mg (0.63 mmol) of 1-[6-fluoro-8-methoxy-3-({[2-methyl-4-(trifluoromethoxy)benzyl]amino}carbonyl)-4-oxo-1-(2,2,2-trifluoroethyl)-1,4-dihydroquinolin-7-yl]piperidine-4-carboxylic acid (Example 47) are suspended in 20 ml of deionized water and 20 ml of acetonitrile at RT. 140 μl (153 mg, 0.63 mmol) of β-hydroxyethyltrimethylammonium hydroxide (“choline hydroxide”) are added and the mixture is stirred at RT overnight. The resulting solution is freed from the acetonitrile on a rotary evaporator. The aqueous solution which remains was frozen and lyophilized. 494 mg (100% of theory) of residue, which is found by analysis to correspond to the title compound, are obtained.

Workup

  1. customat RT
  2. customThe resulting solution is freed from the acetonitrile on a rotary evaporator
  3. temperatureThe aqueous solution which remains was frozen
  4. customare obtained

Sources & evidence

ORD record
ord-88fe8404128f4fb184769a4ee2c158ce
Source dataset
uspto-grants-2011_07
Patent number
US07977349B2

Reaction notes

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