Sodium Bicarbonate → HCID 44517635, compound

HRID 1818739Notes

Reaction equation

HRID 1818739 reaction equation
C(OC([NH:8][N:9]=[C:10]([C:19]1[C:20](OC2C=CC(F)=CC=2F)=[N:21][C:22]([O:25][C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][C:27]=2[F:33])=[N:23][CH:24]=1)[NH:11][C@H:12]([CH3:18])[CH2:13][S:14]([CH3:17])(=[O:16])=[O:15])=O)(C)(C)C.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1.Cl.C(OC(C)C)(=O)C>[F:33][C:27]1[CH:28]=[C:29]([F:32])[CH:30]=[CH:31][C:26]=1[O:25][C:22]1[N:21]=[C:20]2[NH:8][N:9]=[C:10]([NH:11][C@H:12]([CH3:18])[CH2:13][S:14]([CH3:17])(=[O:15])=[O:16])[C:19]2=[CH:24][N:23]=1

Participants

6

Reactant 2

HCID 516892Sodium BicarbonateHCID 178461823HCID 178461823, compound

Product 1

HCID 44517635HCID 44517635, compoundYield 71.4%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 1140TolueneSolventHCID 7915Isopropyl AcetateSolvent

Procedure

A solution of 1.02 kg of N′-[[2,4-bis-(2,4-difluoro-phenoxy)-pyrimidin-5-yl]-((R)-2-methanesulfonyl-1-methyl-ethylamino)-methylene]-hydrazinecarboxylic acid tert-butyl ester in toluene (6-8 l) and conc HCl. (500 ml) was stirred at room temperature overnight. The reaction mixture was diluted with iso-propyl acetate (3.5 L) and a saturated aqueous sodium bicarbonate solution was added. The resulting solid precipitate was collected by filtration, washed with aqueous sodium bicarbonate, water, then with methyl t-butyl ether, and dried under vacuum. The material was recrystallized from isobutanol to give 455 g of [6-(2,4-difluoro-phenoxy)-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-((R)-2-methanesulfonyl-1-methyl-ethyl)-amine. Mp=177.7-178.8° C., MS(M+H)=384.

Workup

  1. filtrationThe resulting solid precipitate was collected by filtration
  2. washwashed with aqueous sodium bicarbonate, water
  3. dry with materialwith methyl t-butyl ether, and dried under vacuum
  4. customThe material was recrystallized from isobutanol

Sources & evidence

ORD record
ord-d34cc1785b124d7bb01cf907da9fb746
Source dataset
uspto-grants-2009_10
Patent number
US07601726B2

Reaction notes

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