1-({3-[(1S,2S)-2-Hydroxycyclohexyl]-4-oxo-3,4-dihydrobenzo[h]quinazolin-6-yl}methyl)-4-pyridin-2-ylpiperidine-4-carbonitrile → 4-Methylpiperidine-4-carbonitrile

HRID 390326Notes

Reaction equation

HRID 390326 reaction equation
O[C@H]1CCCC[C@@H]1N1C(=O)C2C(=C3C=CC=CC3=C(C[N:20]3[CH2:25][CH2:24][C:23]([C:28]4C=CC=CN=4)([C:26]#[N:27])[CH2:22][CH2:21]3)C=2)N=C1.N1C=CC=CC=1C1(C#N)CCNCC1>>[CH3:28][C:23]1([C:26]#[N:27])[CH2:24][CH2:25][NH:20][CH2:21][CH2:22]1

Participants

3

Reactant 2

HCID 532553611-({3-[(1S,2S)-2-Hydroxycyclohexyl]-4-oxo-3,4-dihydrobenzo[h]quinazolin-6-yl}methyl)-4-pyridin-2-ylpiperidine-4-carbonitrileHCID 533632714-(Pyridin-2-yl)piperidine-4-carbonitrile

Product 1

HCID 207111334-Methylpiperidine-4-carbonitrile

Procedure

The title compound was prepared by the procedure described for the synthesis of 1-({3-[(1S,2S)-2-hydroxycyclohexyl]-4-oxo-3,4-dihydrobenzo[h]quinazolin-6-yl}methyl)-4-pyridin-2-ylpiperidine-4-carbonitrile in Example 2, substituting 4-methylpiperidine-4-carbonitrile for 4-pyridin-2-ylpiperidine-4-carbonitrile. The resultant solid gave proton NMR spectra consistent with theory and a mass ion (ES+) of 431.2438 for [M+H]+ [Calc'd for C26H31N4O2, [M+H]+=431.2444]: 1H NMR (400 MHz, CDCl3) δ 8.96-8.93 (m, 1H), 8.28-8.23 (m, 1H), 8.05 (s, 1H), 7.72-7.65 (m, 2H), 4.64 (br s, 1H), 4.04 (br s, 1H), 3.92 (s, 2H), 2.87 (br s, 2H), 2.56-2.53 (m, 1H), 2.45 (d, J=12.2 Hz, 2H), 2.29-2.26 (m, 1H), 2.09-1.86 (m, 5H), 1.64-1.41 (m, 5H), 1.36 (s, 3H).

Workup

  1. customThe resultant solid gave proton NMR spectra consistent with theory

Sources & evidence

ORD record
ord-f78be1cc96494de580d6759c04817414
Source dataset
uspto-grants-2013_02
Patent number
US08383638B2

Reaction notes

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