Methylamine → (R)-3-(5-chloro-1-(5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)spiro[indoline-3,4'-piperidine]-1'-yl)propan-1-amine

HRID 529096Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 529096
[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]3([CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][N:19]4C(=O)C5C(=CC=CC=5)C4=O)[CH2:12][CH2:11]3)[CH2:9][N:8]([C:30]3[C:31]4[C@H:38]([CH3:39])[CH2:37][CH2:36][C:32]=4[N:33]=[CH:34][N:35]=3)[C:5]2=[CH:6][CH:7]=1.CN>CO>[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]3([CH2:11][CH2:12][N:13]([CH2:16][CH2:17][CH2:18][NH2:19])[CH2:14][CH2:15]3)[CH2:9][N:8]([C:30]3[C:31]4[C@H:38]([CH3:39])[CH2:37][CH2:36][C:32]=4[N:33]=[CH:34][N:35]=3)[C:5]2=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 6329MethylamineHCID 68764576(R)-2-(3-(5-chloro-1-(5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)spiro[indoline-3,4'-piperidine]-1'-yl)propyl)isoindoline-1,3-dione

Produkt 1

HCID 44198402(R)-3-(5-chloro-1-(5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)spiro[indoline-3,4'-piperidine]-1'-yl)propan-1-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of (R)-2-(3-(5-chloro-1-(5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)spiro[indoline-3,4′-piperidine]-1′-yl)propyl)isoindoline-1,3-dione (9 mg, 0.02 mmol) and 2M MeNH2 in MeOH (0.5 mL) was stirred at about room temperature overnight. The solvent was evaporated. The residue was purified by column chromatography (DCM:7N ammonia in MeOH, 8:1) to give (R)-3-(5-chloro-1-(5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)spiro[indoline-3,4′-piperidine]-1′-yl)propan-1-amine as a free base, which was taken up in DCM and acidified with 2N HCl in ether. Removal of the solvents under reduced pressure afforded (R)-3-(5-chloro-1-(5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)spiro[indoline-3,4′-piperidine]-1′-yl)propan-1-amine trihydrochloride (5 mg, 74%) as a solid. LCMS (APCI+) m/z 412, 414 [M+H]+; Rt=2.47 min.

Aufarbeitung

  1. customThe solvent was evaporated
  2. customThe residue was purified by column chromatography (DCM:7N ammonia in MeOH, 8:1)

Quellen und Nachweise

ORD-Eintrag
ord-f1e74247df3647db8376246732466bb1
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09346805B2

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