Methylamine → HCID 178482399, compound

HRID 1671757Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6](Cl)[N:5]=[C:4](Cl)[N:3]=1.[CH3:10][NH2:11].C1COCC1.[OH-].[Na+].[CH3:19][NH:20][C@@H:21]1[CH2:26][CH2:25][C@H:24]([C:27]([OH:29])=[O:28])[CH2:23][CH2:22]1.[CH3:30][N:31]1[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1>CC#N.O>[CH3:19][N:20]([C:2]1[N:7]=[C:6]([NH:11][CH3:10])[N:5]=[C:4]([N:34]2[CH2:35][CH2:36][N:31]([CH3:30])[CH2:32][CH2:33]2)[N:3]=1)[C@@H:21]1[CH2:26][CH2:25][C@H:24]([C:27]([OH:29])=[O:28])[CH2:23][CH2:22]1

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of 2,4,6-trichloro-1,3,5-triazine (0.5 g, 2.0 mmol) in a solution of CH3CN:H2O (1:1, 20 mL) was cooled to 0° C. A 2 M solution of methylamine in THF (1 mL, 2.0 mmol) was added. The reaction mixture was adjusted to a pH of about 8-9 using 1 N NaOH. The pH was maintained at about 9-10 for 0.5 hour. LCMS analysis showed the complete consumption of the 2,4,6-trichloro-1,3,5-triazine. To this mixture was added cis-4-(methylamino)cyclohexanecarboxylic acid (0.32 g, 2.0 mmol). The reaction mixture was stirred at room temperature while the pH was maintained between 8 and 9. Next, 1-methylpiperazine (2 g, 20 mmol) was added and the mixture was heated to 50° C. overnight. The solvent was removed and the crude product was purified by HPLC to afford 0.32 g (0.09 mmol, 44% yield) of the desired product. MS (ES+): m/e 364.2 [M+H]+.

Workup

temperatureThe pH was maintained at about 9-10 for 0.5 hour
customthe complete consumption of the 2,4,6-trichloro-1,3,5-triazine
temperaturewas maintained between 8 and 9
temperaturethe mixture was heated to 50° C. overnight
customThe solvent was removed
customthe crude product was purified by HPLC

Sources & evidence

ORD record: ord-27b32fca72d44d9db0b1995339bef2ab
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07994317B2

Reaction notes

Loading…