Water → HCID 58316929, compound

HRID 1187312Notes

Reaction equation

HRID 1187312 reaction equation
Cl[C:2]1[C:3]2[C:10]([C:11]([C:13]3[C:14]([F:33])=[C:15]([NH:20][S:21]([C:24]4[CH:29]=[CH:28][C:27]([CH2:30][CH2:31][CH3:32])=[CH:26][CH:25]=4)(=[O:23])=[O:22])[CH:16]=[CH:17][C:18]=3[F:19])=[O:12])=[CH:9][NH:8][C:4]=2[N:5]=[CH:6][N:7]=1.C(O)(C)C.[CH:38]1([NH2:41])[CH2:40][CH2:39]1.O>[Cl-].[Na+].O>[CH:38]1([NH:41][C:2]2[C:3]3[C:10]([C:11]([C:13]4[C:14]([F:33])=[C:15]([NH:20][S:21]([C:24]5[CH:25]=[CH:26][C:27]([CH2:30][CH2:31][CH3:32])=[CH:28][CH:29]=5)(=[O:22])=[O:23])[CH:16]=[CH:17][C:18]=4[F:19])=[O:12])=[CH:9][NH:8][C:4]=3[N:5]=[CH:6][N:7]=2)[CH2:40][CH2:39]1

Participants

6

Reactant 4

HCID 962WaterHCID 3776IsopropanolHCID 69828CyclopropylamineHCID 53237746HCID 53237746, compound

Product 1

HCID 58316929HCID 58316929, compoundYield 101.7%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
80 °C

Procedure

To N-[3-(4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonyl)-2,4-difluoro-phenyl]-4-propyl-benzenesulfonamide (P-1034, 50 mg, 0.10 mmol), 0.702 mL of isopropyl alcohol is added, followed by cyclopropylamine (79, 0.0357 mL, 70% aqueous solution, 0.509 mmol). The reaction is heated at 80° C. in an oil bath for 17 hours, then poured into water and brine and extracted with ethyl acetate. The organic layer is dried over magnesium sulfate, filtered and the filtrate concentrated under vacuum to provide the desired compound (P-1040, 52 mg). MS (ESI) [M+H+]+=512.0.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer is dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated under vacuum

Sources & evidence

ORD record
ord-3b4935dc76dd486b8c90b99746e977e7
Source dataset
uspto-grants-2014_03
Patent number
US08673928B2

Reaction notes

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