Hydrochloric Acid → 5-(4-fluoro-2,3-dihydro-1H-indol-5-yl)-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine dihydrochloride

HRID 1910043Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1910043
[NH2:1][C:2]1[C:3]2[C:10]([C:11]3[C:12]([F:27])=[C:13]4[C:17](=[CH:18][CH:19]=3)[N:16](C(OC(C)(C)C)=O)[CH2:15][CH2:14]4)=[CH:9][N:8]([CH3:28])[C:4]=2[N:5]=[CH:6][N:7]=1.[ClH:29]>>[ClH:29].[ClH:29].[F:27][C:12]1[C:11]([C:10]2[C:3]3[C:2]([NH2:1])=[N:7][CH:6]=[N:5][C:4]=3[N:8]([CH3:28])[CH:9]=2)=[CH:19][CH:18]=[C:17]2[C:13]=1[CH2:14][CH2:15][NH:16]2

Komponenten

3

Edukt 2

HCID 313Hydrochloric AcidHCID 668236891,1-dimethylethyl 5-(4-amino-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-4-fluoro-2,3-dihydro-1H-indole-1-carboxylate

Produkt 1

HCID 668236155-(4-fluoro-2,3-dihydro-1H-indol-5-yl)-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine dihydrochlorideAusbeute 79 %

Versuchsvorschrift

A suspension of 1,1-dimethylethyl 5-(4-amino-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-4-fluoro-2,3-dihydro-1H-indole-1-carboxylate (430 mg, 1.121 mmol) and HCl (4 M, dioxane) (10 mL, 329 mmol) was stirred at room temperature overnight. LCMS indicated the reaction was complete, so the reaction mixture was filtered and the residue washed with dioxane (10 mL) and dried at the pump for an hour to afford 5-(4-fluoro-2,3-dihydro-1H-indol-5-yl)-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine 2HCl (314 mg, 79% yield) as an off-white solid. LC-MS (ES) m/z=284 [M+H]+. 1H NMR (600 MHz, DMSO-d6) δ ppm 3.14 (t, J=7.93 Hz, 2H), 3.68 (t, J=7.90 Hz, 2H), 3.84 (s, 3H), 6.83 (br. s., 1H), 7.16 (t, J=6.99 Hz, 1H), 7.59 (s, 1H), 8.49 (s, 1H).

Aufarbeitung

  1. filtrationwas filtered
  2. washthe residue washed with dioxane (10 mL)
  3. customdried at the pump for an hour

Quellen und Nachweise

ORD-Eintrag
ord-6b97c28b030f47baa57b3c34869d2e0d
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08598156B2

Notizen zur Reaktion

Wird geladen…