1-Methylpiperazine → 1-Formyl-4-methylpiperazine

Reaction equation

ClC1N=C(N2CCOCC2)C2SC(C3C=C([C:17](O)=[O:18])C=NC=3)=CC=2N=1.[CH3:26][N:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1>>[CH3:26][N:27]1[CH2:32][CH2:31][N:30]([CH:17]=[O:18])[CH2:29][CH2:28]1

Participants

Reactant 2

HCID 531671-Methylpiperazine

HCID 86618438HCID 86618438, compound

Product 1

HCID 32692211-Formyl-4-methylpiperazine

Procedure

5-(2-Chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)pyridine-3-carboxylic acid (40 mg) was reacted with 1-methylpiperizine via General Procedure B to yield 5-(2-chloro-4-morpholinothieno[3,2-d]-pyrimidin-6-yl)pyridine-3-yl)(4-methylpiperazin-1-yl)methanone. Crude 5-(2-chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)pyridine-3-yl)(4-methylpiperazin-1-yl)methanone (48 mg) was coupled to 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole 7 via General Procedure A to yield 14.6 mg of 348. MS (Q1) 541.1 (M)+

Sources & evidence

ORD record: ord-fa57c0c50fd4424888f6154a009bb32a
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08450315B2

Reaction notes

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