4-Methoxypiperidine → HCID 67020640, compound

HRID 550525Notes

Reaction equation

CS(O[CH2:6][CH2:7][O:8][C:9]1[C:17]2[C:12](=[N:13][CH:14]=[N:15][C:16]=2[NH:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[C:21]([CH3:33])[CH:20]=2)[NH:11][N:10]=1)(=O)=O.[CH3:34][O:35][CH:36]1[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]1>>[CH2:26]([O:25][C:22]1[CH:23]=[CH:24][C:19]([NH:18][C:16]2[N:15]=[CH:14][N:13]=[C:12]3[NH:11][N:10]=[C:9]([O:8][CH2:7][CH2:6][N:39]4[CH2:40][CH2:41][CH:36]([O:35][CH3:34])[CH2:37][CH2:38]4)[C:17]=23)=[CH:20][C:21]=1[CH3:33])[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

Reactant 2

HCID 776664-Methoxypiperidine

HCID 86620009HCID 86620009, compound

Product 1

HCID 67020640HCID 67020640, compoundYield 37%

Procedure

The procedure described in Example 55 was repeated using 2-[(4-{[4-(benzyloxy)-3-methylphenyl]amino}-1H-pyrazolo[3,4-d]pyrimidin-3-yl)oxy]ethyl methanesulfonate (prepared as described in Example 110) and 4-methoxypiperidine (prepared as described in Example 118, starting material) to give the title compound in 37% yield; NMR Spectrum: 1.37-1.43 (m, 2H), 1.78-1.81 (m, 2H), 2.18-2.22 (m, 2H), 2.22 (s, 3H), 2.75-2.78 (m, 4H), 3.12-3.16 (m, 1H), 3.20 (s, 3H), 4.40 (t, 2H), 5.13 (s, 2H), 7.01 (d, 1H), 7.31-7.48 (m, 7H), 8.23 (s, 1H), 8.32 (s, 1H); Mass Spectrum: 489 (MH+).

Sources & evidence

ORD record: ord-fea413902d574bd88592298228f3fbdc
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07947676B2

Reaction notes

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