N-Methylcyclohexylamine → HCID 10111866, compound

HRID 966527Notes

Reaction equation

[CH2:1]([O:8][C:9]([C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([CH2:20][CH2:21]OS(C)(=O)=O)[CH:18]=2)[NH:13][C:12]=1[CH3:27])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:28][NH:29][CH:30]1[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1>O1CCOCC1>[CH2:1]([O:8][C:9]([C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([CH2:20][CH2:21][N:29]([CH:30]3[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]3)[CH3:28])[CH:18]=2)[NH:13][C:12]=1[CH3:27])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 5-(2-methanesulfonyloxy-ethyl)-2-methyl-1H-indole-3-carboxylic acid benzyl ester (400 mg, 1.03 mmol, Example 56, Step D) in dioxane (10 mL) was added N-methylcyclohexylamine (1.3 mL, 10.3 mmol). The mixture was stirred at 80° C. overnight and then partitioned between methylene chloride and water. The organic phase was washed with water and brine, dried over Na2SO4 and filtered. The filtrate was concentrated in vacuo to give a solid residue, which was purified by chromatography (5%-15% methanol in methylene chloride) to give 250 mg (60%) of the desired product as a white solid: mp 122-124° C.; MS(APCI+): m/z 405.2 (MH+); Anal. Calcd for C26H32N2O2.0.5H2O: C, 75.51; H, 8.04; N, 6.77. Found: C, 75.25; H, 8.04; N, 6.78.

Workup

custompartitioned between methylene chloride and water
washThe organic phase was washed with water and brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationThe filtrate was concentrated in vacuo
customto give a solid residue, which
customwas purified by chromatography (5%-15% methanol in methylene chloride)

Sources & evidence

ORD record: ord-df7245defb584c0fbf7d6d6b71e33659
Source dataset: uspto-grants-2005_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06951848B2

Reaction notes

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