Potassium Carbonate → HCID 66931862, compound

HRID 1958832Notes

Reaction equation

Br[CH2:2][CH2:3][CH2:4][OH:5].[CH2:6]([C:8]1[CH:13]=[C:12]([C:14]2[N:18]=[C:17]([C:19]3[CH:24]=[C:23]([CH3:25])[CH:22]=[C:21]([CH2:26][N:27]([CH2:29][CH3:30])[CH3:28])[CH:20]=3)[O:16][N:15]=2)[CH:11]=[C:10]([CH3:31])[C:9]=1[OH:32])[CH3:7].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH2:6]([C:8]1[CH:13]=[C:12]([C:14]2[N:18]=[C:17]([C:19]3[CH:24]=[C:23]([CH3:25])[CH:22]=[C:21]([CH2:26][N:27]([CH2:29][CH3:30])[CH3:28])[CH:20]=3)[O:16][N:15]=2)[CH:11]=[C:10]([CH3:31])[C:9]=1[O:32][CH2:2][CH2:3][CH2:4][OH:5])[CH3:7]

Participants

Conditions

Temperature: 60 °C

Procedure

3-bromo-1-propanol (55 mg, 398 μmol) was added to a suspension of 2-ethyl-4-(5-{3-[(ethyl-methyl-amino)-methyl]-5-methyl-phenyl}-[1,2,4]oxadiazol-3-yl)-6-methyl-phenol (97 mg, 265 μmol) and K2CO3 (88 mg, 637 μmol) in DMF (2 mL). The mixture was stirred at 60° C. for 3 h before it was filtered. The filtrate was separated by prep. HPLC (XBridge 30×75 mm, eluting with a gradient of MeCN in water containing 0.5% of sat. aq. ammonia) to give the title compound as a colourless resin (67 mg). LC-MS**: tR=0.61 min; [M+1]+=424.25; 1H NMR (D6-DMSO): δ 1.06 (t, J=7.0 Hz, 3H), 1.23 (t, J=7.3 Hz, 3H), 1.90-1.98 (m, 2H), 2.15 (s, 3H), 2.34 (s, 3H), 2.41-2.49 (m, 5H), 2.71 (q, J=7.3 Hz, 2H), 3.55 (s, 2H), 3.65 (q, J=5.8 Hz, 2H), 3.90 (t, J=6.0 Hz, 2H), 4.55 (t, J=4.8 Hz, 1H), 7.47 (s, 1H), 7.80 (s, 2H), 7.90 (s, 1H), 7.92 (s, 1H).

Workup

filtrationwas filtered
customThe filtrate was separated by prep
washHPLC (XBridge 30×75 mm, eluting with a gradient of MeCN in water containing 0.5% of sat. aq. ammonia)

Sources & evidence

ORD record: ord-2f80add70bc44fc59f8b522d96788735
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08410151B2

Reaction notes

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