HCID 135474385, compound → HCID 136090339, compound

HRID 131461Notes

Reaction equation

[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[C:17]3[CH:16]=[C:15]([CH3:18])[S:14][C:13]=3[NH:12][C:11]3[CH:19]=[CH:20][CH:21]=[CH:22][C:10]=3[N:9]=2)[CH2:4][C@@H:3]1[CH2:23][OH:24].[CH3:25]OC[C@@H]1NCCN(C2C3C=C(C)SC=3NC3C=CC=CC=3N=2)C1>>[CH3:25][O:24][CH2:23][C@@H:3]1[N:2]([CH3:1])[CH2:7][CH2:6][N:5]([C:8]2[C:17]3[CH:16]=[C:15]([CH3:18])[S:14][C:13]=3[NH:12][C:11]3[CH:19]=[CH:20][CH:21]=[CH:22][C:10]=3[N:9]=2)[CH2:4]1

Participants

Reactant 2

HCID 135474385HCID 135474385, compound

HCID 135517319HCID 135517319, compound

Product 1

HCID 136090339HCID 136090339, compound

Procedure

Using a similar method to (R)-[1-methyl-4-(2-methyl-4H-3-thia-4,9-diaza-benzo[f]azulen-10-yl)-piperazin-2-yl]-methanol, using (R)-10-(3-methoxymethyl-piperazin-1-yl)-2-methyl-4H-3-thia-4,9-diaza-benzo[f]azulene (800 mg) affords the title compound as a yellow solid (758 mg): mp 76-80° C.; 1H NMR (CDCl3) δ 2.31 (s, 3H), 2.42-2.27 (m, 2H), 2.39 (s, 3H), 2.84 (dt, 1H), 2.99 (dd, 1H), 3.14 (ddd, 1H), 3.36 (s, 3H), 3.46 (dd, 1H), 3.54 (dd, 1H), 3.91 (d, 1H), 4.02 (d, 1H), 4.96 (s, 1H), 6.30 (d, 1H), 6.60 (dd, 1H), 6.87 (dt, 1H), 6.96 (dt, 1H), 7.04 (dd, 1H); MS (APCI) m/z (rel intensity) 357.2 (100).

Sources & evidence

ORD record: ord-c5ba0e416ee4412d922f419af5d92f97
Source dataset: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07384934B2

Reaction notes

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