Water → Golvatinib Tartrate

HRID 2066325Notes

Reaction equation

HRID 2066325 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH:15][C:16]([N:18]3[CH2:23][CH2:22][CH:21]([N:24]4[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]4)[CH2:20][CH2:19]3)=[O:17])[CH:10]=2)[CH:5]=[CH:4][C:3]=1[NH:31][C:32]([C:34]1([C:37]([NH:39][C:40]2[CH:45]=[CH:44][C:43]([F:46])=[CH:42][CH:41]=2)=[O:38])[CH2:36][CH2:35]1)=[O:33].[C:47]([OH:56])(=[O:55])[C@@H:48]([C@H:50]([C:52]([OH:54])=[O:53])[OH:51])[OH:49].O>C(O)C>[C:47]([OH:56])(=[O:55])[C@@H:48]([C@H:50]([C:52]([OH:54])=[O:53])[OH:51])[OH:49].[F:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH:15][C:16]([N:18]3[CH2:19][CH2:20][CH:21]([N:24]4[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]4)[CH2:22][CH2:23]3)=[O:17])[CH:10]=2)[CH:5]=[CH:4][C:3]=1[NH:31][C:32]([C:34]1([C:37]([NH:39][C:40]2[CH:41]=[CH:42][C:43]([F:46])=[CH:44][CH:45]=2)=[O:38])[CH2:36][CH2:35]1)=[O:33]

Participants

5

Reactant 3

HCID 962WaterHCID 444305L-Tartaric acidHCID 16118392Golvatinib

Product 1

HCID 24771321Golvatinib TartrateYield 85.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
50 °C

Procedure

N-(2-Fluoro-4-{[2-({[4-(4-methylpiperazin-1-yl)piperidin-1-yl]carbonyl}amino)pyridin-4-yl]oxy}phenyl)-N′-(4-fluorophenyl)cyclopropane-1,1-dicarboxamide (63.4 mg) was suspended in ethanol (1.168 ml). To this was added a 1M solution of L-(+)-tartaric acid in ethanol (0.100 ml), followed by heating at 50° C. Water (0.1268 ml) was added thereto to dissolve completely. The reaction mixture was stirred at 50° C. for 1 hr and 45 min, then stirred overnight while allowing it to gradually cool down to room temperature. Insoluble matter was collected by filtration and washed with ethanol (0.200 ml). This was dried under aeration at room temperature to provide the titled compound as colorless crystals (66.7 mg, 85.1%).

Workup

  1. dissolutionto dissolve completely
  2. stirringstirred overnight
  3. temperatureto gradually cool down to room temperature
  4. filtrationInsoluble matter was collected by filtration
  5. washwashed with ethanol (0.200 ml)
  6. customThis was dried under aeration at room temperature

Sources & evidence

ORD record
ord-9b9958a7aaf24a109e532105d4da42c5
Source dataset
uspto-grants-2012_10
Patent number
US08288538B2

Reaction notes

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