Sodium Hydroxide → N-(3-chloro-4-methoxyphenyl)-N'-cycloheptyl-6-(1-ethylpiperidin-3-yloxy)-[1,3,5]triazine-2,4-diamine

HRID 2057054Notes

Reaction equation

[CH2:1]([N:3]1[CH2:8][CH2:7][CH2:6][CH:5]([OH:9])[CH2:4]1)[CH3:2].[OH-].[Na+].Cl[C:13]1[N:18]=[C:17]([NH:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([Cl:28])[CH:21]=2)[N:16]=[C:15]([NH:29][CH:30]2[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]2)[N:14]=1>C1C=CC=CC=1>[Cl:28][C:22]1[CH:21]=[C:20]([NH:19][C:17]2[N:16]=[C:15]([NH:29][CH:30]3[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36]3)[N:14]=[C:13]([O:9][CH:5]3[CH2:6][CH2:7][CH2:8][N:3]([CH2:1][CH3:2])[CH2:4]3)[N:18]=2)[CH:25]=[CH:24][C:23]=1[O:26][CH3:27]

Participants

Conditions

Temperature: 25 °C

Procedure

A mixture of N-ethyl-3-hydroxypiperidine (0.3 g, 2.3 mmol) and NaOH (94 mg, 2.3 mmol) in benzene (10 ml) was heated to reflux for 2 hr with stirring under nitrogen atmosphere and then cooled to 25° C. followed by the addition of compound 133 (0.3 g, 0.78 mmol) at same temperature. The mixture was heated to reflux for 12 hrs., concentrated under vacuum and diluted with water (10 ml). The solid precipitated was filtered off and washed with petroleum ether to afford the title compound as a off white solid (0.3 g, 81%). mp 62-64° C.; HPLC: HICHROM RPB (250×4.6 mm) 5 microns [solvent A=0.01 M KH2PO4 (pH 6.0); solvent B=CH3CN], Gradient elution program: T/% B=0/40, 5/40, 25/80, 35/80, 40/40, 45/40; 270 nm, Rt 26.83 min, 93.65% purity; MS (CI): m/z 447 (M+, 100).

Workup

temperaturewas heated
temperatureto reflux for 2 hr
temperatureThe mixture was heated
temperatureto reflux for 12 hrs
concentration, concentrated under vacuum
additiondiluted with water (10 ml)
customThe solid precipitated
filtrationwas filtered off
washwashed with petroleum ether

Sources & evidence

ORD record: ord-1625ca4f98eb4822a0872eed8b0d26f0
Source dataset: uspto-grants-2008_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07335770B2

Reaction notes

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