Benzenesulfonic Acid → 2-chloro-3-(1-cyano-1-methylethoxy)-N-{5-[{2-[(cyclopropylcarbonyl)amino][1,3]thiazolo[5,4-b]pyridin-5-yl}(methyl)amino]-2-fluorophenyl}benzamide benzenesulfonate

HRID 1800642Notes

Reaction equation

HRID 1800642 reaction equation
[Cl:1][C:2]1[C:34]([O:35][C:36]([C:39]#[N:40])([CH3:38])[CH3:37])=[CH:33][CH:32]=[CH:31][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[C:11]([N:13]([C:15]2[N:20]=[C:19]3[S:21][C:22]([NH:24][C:25]([CH:27]4[CH2:29][CH2:28]4)=[O:26])=[N:23][C:18]3=[CH:17][CH:16]=2)[CH3:14])[CH:10]=[CH:9][C:8]=1[F:30])=[O:5].[C:41]1([S:47]([OH:50])(=[O:49])=[O:48])[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1.O1CCCC1.CCCCCCC>C(OCC)(=O)C>[C:41]1([S:47]([OH:50])(=[O:49])=[O:48])[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1.[Cl:1][C:2]1[C:34]([O:35][C:36]([C:39]#[N:40])([CH3:38])[CH3:37])=[CH:33][CH:32]=[CH:31][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[C:11]([N:13]([C:15]2[N:20]=[C:19]3[S:21][C:22]([NH:24][C:25]([CH:27]4[CH2:29][CH2:28]4)=[O:26])=[N:23][C:18]3=[CH:17][CH:16]=2)[CH3:14])[CH:10]=[CH:9][C:8]=1[F:30])=[O:5]

Participants

6

Reactant 4

HCID 7371Benzenesulfonic AcidHCID 8028TetrahydrofuranHCID 8900HeptaneHCID 252063462-Chloro-3-[(2-Cyanopropan-2-Yl)oxy]-N-{5-[{2-[(Cyclopropylcarbonyl)amino][1,3]thiazolo[5,4-B]pyridin-5-Yl}(Methyl)amino]-2-Fluorophenyl}benzamide

Product 1

HCID 252065002-chloro-3-(1-cyano-1-methylethoxy)-N-{5-[{2-[(cyclopropylcarbonyl)amino][1,3]thiazolo[5,4-b]pyridin-5-yl}(methyl)amino]-2-fluorophenyl}benzamide benzenesulfonateYield 80%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

2-Chloro-3-(1-cyano-1-methylethoxy)-N-{5-[(2-[(cyclopropylcarbonyl)amino][1,3]thiazolo[5,4-b]pyridin-5-yl}(methyl)amino]-2-fluorophenyl)benzamide (150 mg, 0.259 mmol) produced in Example C122(xi) was dissolved in ethyl acetate (4 mL), and benzenesulfonic acid (185 mg, 1.05 mmol) was added. Tetrahydrofuran was added while stirring the obtained mixture at 50° C. to give a yellow solution, and the solution was stirred at 50° C. for 15 min. The solution was concentrated under reduced pressure, and tetrahydrofuran (4 mL) was added to the obtained oily residue to give a solution. Heptane was added at 50° C. to give a saturated solution, and the solution was cooled to room temperature. The crystallized crystals were collected by filtration, and dried to give the title compound (152 mg, 80%) as colorless crystals.

Workup

  1. customto give a yellow solution
  2. stirringthe solution was stirred at 50° C. for 15 min
  3. concentrationThe solution was concentrated under reduced pressure, and tetrahydrofuran (4 mL)
  4. additionwas added to the obtained oily residue
  5. customto give a solution
  6. customto give a saturated solution
  7. temperaturethe solution was cooled to room temperature
  8. filtrationThe crystallized crystals were collected by filtration
  9. customdried

Sources & evidence

ORD record
ord-52b7c841cbbe4505833a9664e9e5feb2
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

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