Potassium Carbonate → HCID 59837526, compound

HRID 273072Notes

Reaction equation

[O:1]1[CH2:7][CH2:6][CH2:5][N:4]([CH2:8][CH2:9][CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3([CH2:24][NH2:25])[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)=[CH:14][CH:13]=2)[CH2:3][CH2:2]1.Br[CH2:27][CH2:28][O:29][CH2:30][CH2:31]Br.C([O-])([O-])=O.[K+].[K+]>C(#N)C>[NH3:4].[N:25]1([CH2:24][C:18]2([C:15]3[CH:16]=[CH:17][C:12]([O:11][CH2:10][CH2:9][CH2:8][N:4]4[CH2:5][CH2:6][CH2:7][O:1][CH2:2][CH2:3]4)=[CH:13][CH:14]=3)[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1

Participants

Conditions

Temperature: 60 °C

Procedure

C-{4-[4-(3-[1,4]Oxazepan-4-yl-propoxy)-phenyl]-tetrahydro-pyran-4-yl}-methylamine (150 mg, 0.43 mmol) and 1-Bromo-2-(2-bromo-ethoxy)-ethane (110 mg, 0.47 mmol) were dissolved in acetonitrile (10 ml) and K2CO3 (130 mg, 0.95 mmol) was added. The solution was heated at 60° C. for 18 hours before filtering the solution to remove to the solid K2CO3. The filtrate was concentrated in vacuo before purifying using column chromatography, eluting with a gradient of DCM:MeOH:NH3 (from 99:1:0.1 to 90:10:1) to afford the title compound as a colourless oil (75 mg, 42%). 1H NMR (400 MHz, CD3OD) δ 1.80-2.00 (m, 6H), 2.11-2.20 (m, 6H), 2.41 (s, 2H), 2.69-2.79 (m, 6H), 3.48 (m, 6H), 3.72-3.80 (m, 6H), 4.02 (t, 2H), 6.87 (d, 2H), 7.15 (d, 2H). HRMS ESI+ m/z 419.2896 [MH]+.

Workup

filtrationbefore filtering the solution
customto remove to the solid K2CO3
concentrationThe filtrate was concentrated in vacuo
custombefore purifying
washeluting with a gradient of DCM

Sources & evidence

ORD record: ord-01951e0aeab047a793d8989786d72678
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07456164B2

Reaction notes

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