1,4-Dioxane hydrochloride → HCID 24999762, compound

HRID 424140Notes

Reaction equation

HRID 424140 reaction equation
[P:1]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([N:21]2[C:25]([NH:26][C:27](=[O:47])[NH:28][C:29]3[CH:34]=[CH:33][C:32]([O:35][C:36]4[CH:41]=[CH:40][N:39]=[C:38]([C:42](=[O:45])[NH:43][CH3:44])[CH:37]=4)=[CH:31][C:30]=3[F:46])=[CH:24][C:23]([C:48]([CH3:51])([CH3:50])[CH3:49])=[N:22]2)[CH:16]=1)([O:8]C(C)(C)C)([O:3]C(C)(C)C)=[O:2].[ClH:52].O1CCOCC1>O1CCOCC1.CCOCC>[ClH:52].[ClH:52].[P:1]([OH:8])([OH:3])([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([N:21]2[C:25]([NH:26][C:27](=[O:47])[NH:28][C:29]3[CH:34]=[CH:33][C:32]([O:35][C:36]4[CH:41]=[CH:40][N:39]=[C:38]([C:42](=[O:45])[NH:43][CH3:44])[CH:37]=4)=[CH:31][C:30]=3[F:46])=[CH:24][C:23]([C:48]([CH3:49])([CH3:51])[CH3:50])=[N:22]2)[CH:16]=1)=[O:2]

Participants

5

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 24999761HCID 24999761, compound2×

Product 1

HCID 24999762HCID 24999762, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

To a room temperature solution of example 12, di-tert-butyl 3-(3-tert-butyl-5-{[(2-fluoro-4-{[2-(methylcarbamoyl)pyridin-4-yl]oxy}phenyl)carbamoyl]amino}-1H-pyrazol-1-yl)benzyl phosphate, (0.45 g, 0.62 mmol) in dioxane (12 mL) was slowly added HCl/dioxane (4M, 4 mL, 16 mmol). A white precipitate formed and the suspension was stirred at room temperature for 3 h. The reaction mixture was diluted with ether (20 mL) and the solids were collected. The resulting solids were washed with ether followed by hexanes to afford 0.40 g (94%) of the desired product as a white powder. MS m/z 612.9 (M+H)+; Retention time (LC-MS): 3.05 min.

Workup

  1. customTo a room temperature
  2. customA white precipitate formed
  3. customthe solids were collected
  4. washThe resulting solids were washed with ether

Sources & evidence

ORD record
ord-bfc702d94187474087a0eca413fb7bab
Source dataset
uspto-grants-2012_01
Patent number
US08101773B2

Reaction notes

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