Hydrochloric Acid → 4-amino-N-(1-(4-chlorophenyl)-3-sulfamoylpropyl)-1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamide

HRID 423018Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 423018
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([NH:16][C:17]([C:19]2([NH:34]C(=O)OC(C)(C)C)[CH2:24][CH2:23][N:22]([C:25]3[C:26]4[CH:33]=[CH:32][NH:31][C:27]=4[N:28]=[CH:29][N:30]=3)[CH2:21][CH2:20]2)=[O:18])[CH2:10][CH2:11][S:12](=[O:15])(=[O:14])[NH2:13])=[CH:5][CH:4]=1>C(Cl)Cl.CO>[NH2:34][C:19]1([C:17]([NH:16][CH:9]([C:6]2[CH:5]=[CH:4][C:3]([Cl:2])=[CH:8][CH:7]=2)[CH2:10][CH2:11][S:12](=[O:14])(=[O:15])[NH2:13])=[O:18])[CH2:20][CH2:21][N:22]([C:25]2[C:26]3[CH:33]=[CH:32][NH:31][C:27]=3[N:28]=[CH:29][N:30]=2)[CH2:23][CH2:24]1

Komponenten

5

Edukt 2

HCID 313Hydrochloric AcidHCID 57750304tert-butyl 4-(1-(4-chlorophenyl)-3-sulfamoylpropylcarbamoyl)-1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidin-4-ylcarbamate2×

Produkt 1

HCID 577503814-amino-N-(1-(4-chlorophenyl)-3-sulfamoylpropyl)-1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamideAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
22 °C

Versuchsvorschrift

Hydrogen chloride (4M in dioxane, 0.676 mL, 2.70 mmol) was added to tert-butyl 4-(1-(4-chlorophenyl)-3-sulfamoylpropylcarbamoyl)-1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidin-4-ylcarbamate (Intermediate 105) (16 mg, 0.03 mmol) in a mixture of DCM (5 mL) and methanol (5 mL) at 22° C. The resulting solution was stirred at 22° C. for 20 hours. The mixture was evaporated and the residue was purified by ion exchange chromatography, using an SCX column. The desired product was eluted from the column using 30% (2M NH3 in MeOH) in DCM and pure fractions were evaporated to dryness to afford 4-amino-N-(1-(4-chlorophenyl)-3-sulfamoylpropyl)-1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamide (12.00 mg, 90%) as a colourless gum.

Aufarbeitung

  1. customThe mixture was evaporated
  2. customthe residue was purified by ion exchange chromatography
  3. washThe desired product was eluted from the column
  4. custompure fractions were evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-9fb600235f194a8cbc2563c18404bfd2
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08101623B2

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