Pyridine → N1-[4-(4-amino-7-tetrahydro-2H-4-pyranyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methoxyphenyl]benzamide

HRID 51557

Reaktionsgleichung

Reaktionsgleichung von HRID 51557
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:15]([NH2:17])=[N:14][CH:13]=[N:12][C:11]=3[N:10]([CH:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)[CH:9]=2)=[CH:4][C:3]=1[O:24][CH3:25].N1C=CC=C[CH:27]=1.Cl.N1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[C:39](Cl)=[O:40]>ClCCl>[NH2:17][C:15]1[C:16]2[C:8]([C:5]3[CH:6]=[CH:7][C:2]([NH:1][C:39](=[O:40])[C:34]4[CH:27]=[CH:38][CH:37]=[CH:36][CH:35]=4)=[C:3]([O:24][CH3:25])[CH:4]=3)=[CH:9][N:10]([CH:18]3[CH2:19][CH2:20][O:21][CH2:22][CH2:23]3)[C:11]=2[N:12]=[CH:13][N:14]=1

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 135033Picolinoyl Chloride HydrochlorideHCID 227363445-(4-amino-3-methoxyphenyl)-7-tetrahydro-2H-4-pyranyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine

Produkt 1

HCID 69920162N1-[4-(4-amino-7-tetrahydro-2H-4-pyranyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methoxyphenyl]benzamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

5-(4-Amino-3-methoxyphenyl)-7-tetrahydro-2H-4-pyranyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine (80 mg, 0.236 mmol) was dissolved in dichloromethane (2.0 mL). Pyridine (2.0 mL) was added followed by 2-pyridinecarbonyl chloride hydrochloride (63 mg, 0.353 mmol). After stirring at room temperature for 2 hours, the solvent was removed and the residue was dissolved in 1 ml DMSO, methanol (1 mL) was added and precipitate was formed. The solid was collected by filtration to give N1-[4-(4-amino-7-tetrahydro-2H-4-pyranyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methoxyphenyl]benzamide (84 mg, 0.189 mmol). 1H NMR (CDCl3-d) δ 2.12(m, 4H), 3.67(m, 2H), 4.03(s, 3H), 4.14(m, 2H), 5.00(m, 1H), 5.37(s, 1H), 7.04(s, 1H), 7.09(s, 1H), 7.14(d, J=8.2 Hz, 1H), 7.50(m, 1H), 7.92(m, 1H), 8.33(s, 1H), 8.70(d, J=8.2 Hz, 1H), 10.62(s, 1H). LC/MS: MH+=445.

Aufarbeitung

  1. customthe solvent was removed
  2. dissolutionthe residue was dissolved in 1 ml DMSO
  3. additionmethanol (1 mL) was added
  4. customprecipitate was formed
  5. filtrationThe solid was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-4627bf739bd04bddaee335f3af0f9fd3
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06713474B2

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