Water → N-{2-[3-(Aminomethyl)benzyl]-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl}-5-chloro-2-thiophenecarboxamide

HRID 585511Notes

Reaction equation

HRID 585511 reaction equation
C(O)(C(F)(F)F)=O.O.[Cl:9][C:10]1[S:14][C:13]([C:15]([NH:17][C:18]2[CH:26]=[CH:25][CH:24]=[C:23]3[C:19]=2[C:20](=[O:44])[N:21]([CH2:28][C:29]2[CH:30]=[C:31]([CH:41]=[CH:42][CH:43]=2)[CH2:32][NH:33]C(=O)OC(C)(C)C)[C:22]3=[O:27])=[O:16])=[CH:12][CH:11]=1>C(Cl)(Cl)Cl>[NH2:33][CH2:32][C:31]1[CH:30]=[C:29]([CH:43]=[CH:42][CH:41]=1)[CH2:28][N:21]1[C:20](=[O:44])[C:19]2[C:23](=[CH:24][CH:25]=[CH:26][C:18]=2[NH:17][C:15]([C:13]2[S:14][C:10]([Cl:9])=[CH:11][CH:12]=2)=[O:16])[C:22]1=[O:27]

Participants

5

Reactant 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 22337050tert-Butyl 3-[(4-{[(5-chloro-2-thienyl)carbonyl]amino}-1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]benzylcarbamate

Product 1

HCID 22337012N-{2-[3-(Aminomethyl)benzyl]-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl}-5-chloro-2-thiophenecarboxamide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

40 ml of a mixture of TFA and water (9:1) are added dropwise to an ice-cooled mixture of 3.95 g (7.5 mmol) of tert-butyl 3-[(4-{[(5-chloro-2-thienyl)carbonyl]amino}-1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]benzylcarbamate in 40 ml of chloroform. Ice-cooling is removed and the solution is stirred at room temperature for 2 h and then concentrated. The residue is taken up in dichloromethane/methanol (98:2) and the mixture is washed with sat. sodium bicarbonate solution, dried over magnesium sulfate and concentrated. Yield: 3.22 g (97.8% of theory);

Workup

  1. temperaturecooled
  2. temperatureIce-cooling
  3. customis removed
  4. concentrationconcentrated
  5. washthe mixture is washed with sat. sodium bicarbonate solution
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-3b55de77ddfb423dbe46cbdd4deb410b
Source dataset
uspto-grants-2005_08
Patent number
US06933295B2

Reaction notes

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