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

HRID 390322Notes

Reaction equation

HRID 390322 reaction equation
O[C@H]1CCCC[C@@H]1N1C(=O)C2C(=C3C=CC=CC3=C(CN3CCC(C4C=CC=CN=4)(C#N)CC3)C=2)N=C1.[O:38]=[C:39]1[C:48]2[C:43](=[C:44]3[CH:54]=[CH:53][N:52]=[CH:51][C:45]3=[C:46]([CH:49]=O)[CH:47]=2)[N:42]=[CH:41][NH:40]1.[OH:55][C@H:56]1[CH2:61][CH2:60][CH2:59][CH2:58][C@@H:57]1N1C(=O)C2C(=C3C=CC=CC3=C(C=O)C=2)N=C1.[CH3:79][C:80]1[CH:85]=[CH:84][N:83]=[C:82]([C:86]2([C:92]#[N:93])[CH2:91][CH2:90][NH:89][CH2:88][CH2:87]2)[CH:81]=1.N1C=CC=CC=1C1(C#N)CCNCC1>>[OH:55][C@H:56]1[CH2:57][CH2:58][CH2:59][CH2:60][C@@H:61]1[N:40]1[C:39](=[O:38])[C:48]2[C:43](=[C:44]3[CH:54]=[CH:53][N:52]=[CH:51][C:45]3=[C:46]([CH2:49][N:89]3[CH2:90][CH2:91][C:86]([C:82]4[CH:81]=[C:80]([CH3:79])[CH:85]=[CH:84][N:83]=4)([C:92]#[N:93])[CH2:87][CH2:88]3)[CH:47]=2)[N:42]=[CH:41]1

Participants

6

Reactant 5

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-carbonitrileHCID 533632764-(4-Methylpyridin-2-yl)piperidine-4-carbonitrileHCID 866724853-[(1S,2S)-2-hydroxycyclohexyl]-4-oxo-3,4-dihydrobenzo[h]quinazoline-6-carbaldehydeHCID 1364140764-Oxo-3,4-dihydropyrido[3,4-h]quinazoline-6-carbaldehyde

Product 1

HCID 533036591-({3-[(1S,2S)-2-Hydroxycyclohexyl]-4-oxo-3,4-dihydropyrido[3,4-h]quinazolin-6-yl}methyl)-4-(4-methylpyridin-2-yl)piperidine-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 34(1S,2S)-2-hydroxycyclohexyl]-4-oxo-3,4-dihydropyrido[3,4-h]quinazoline-6-carbaldehyde for 3-[(1S,2S)-2-hydroxycyclohexyl]-4-oxo-3,4-dihydrobenzo[h]quinazoline-6-carbaldehyde and 4-(4-methylpyridin-2-yl)piperidine-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 509.0 for [M+H]+: 1H NMR (400 MHz, CD3OD) δ 9.89 (s, 1H), 9.07 (s, 1H), 8.88 (s, 1H), 8.72 (s, 1H), 8.63 (s, 1H), 8.49-8.43 (m, 1H), 7.54 (s, 2H), 7.25-7.13 (m, 1H), 5.09 (s, 2H), 4.16 (br s, 1H), 3.74-3.62 (m, 2H), 3.48-3.41 (m, 2H), 2.65-2.44 (m, 6H), 2.42 (s, 3H), 2.20 (br s, 1H), 2.03-1.93 (m, 1H), 1.88 (br s, 2H), 1.51 (br s, 3H).

Workup

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

Sources & evidence

ORD record
ord-f0f84ad6a0d346d685cc0dcac4e741b5
Source dataset
uspto-grants-2013_02
Patent number
US08383638B2

Reaction notes

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