Dichloromethane → HCID 58728436, compound

HRID 1992188Notes

Reaction equation

Cl.Cl.[CH3:3][C:4]1[N:8]([CH:9]2[CH2:15][C@H:14]3[N:16]([CH2:17][CH2:18][C:19]4([C:25]5[CH:26]=[C:27]([CH2:31][OH:32])[CH:28]=[CH:29][CH:30]=5)[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]4)[C@H:11]([CH2:12][CH2:13]3)[CH2:10]2)[C:7]2[CH:33]=[CH:34][CH:35]=[CH:36][C:6]=2[N:5]=1.CC(C)C[C:40](Cl)=[O:41].CCN([CH:50]([CH3:52])[CH3:51])C(C)C.[CH2:53](Cl)Cl>>[CH3:51][C:50]([CH3:52])([CH3:53])[C:40]([N:22]1[CH2:23][CH2:24][C:19]([C:25]2[CH:26]=[C:27]([CH2:31][OH:32])[CH:28]=[CH:29][CH:30]=2)([CH2:18][CH2:17][N:16]2[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[CH2:15][CH:9]([N:8]2[C:7]4[CH:33]=[CH:34][CH:35]=[CH:36][C:6]=4[N:5]=[C:4]2[CH3:3])[CH2:10]3)[CH2:20][CH2:21]1)=[O:41]

Participants

Reactant 4

HCID 6344Dichloromethane

HCID 66054Isovaleryl chloride

HCID 81531Diisopropylethylamine

HCID 68678796HCID 68678796, compound

Product 1

HCID 58728436HCID 58728436, compoundYield 71%

Procedure

[3-(4-{2-[(1R,5S)-3-(2-methyl-1H-benzimidazol-1-yl)-8-azabicyclo[3.2.1]oct-8-yl]ethyl}-4-piperidinyl) phenyl]methanol dihydrochloride (0.100 g, 0.188 mmol), Dimethyl-propionyl chloride (0.024 g, 0.188 mmol) and DIEA (0.069 g, 0.534 mmol) were stirred at room temperature in DCM (3 ml) for 2 hours. Solvent was removed and compound was purified by RP-HPLC to give the title compound, [3-(1-(2,2-dimethylpropanoyl)-4-{2-[(1R,5S)-3-(2-methyl-1H-benzimidazol-1-yl)-8-azabicyclo[3.2.1]oct-8-yl]ethyl}-4-piperidinyl)phenyl]methanol (0.069 g, 71%). ES-LCMS m/z 543 (M+1).

Workup

customSolvent was removed
customcompound was purified by RP-HPLC

Sources & evidence

ORD record: ord-f0dfcc053da04a20a60b677f34f46c98
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07645771B2

Reaction notes

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