Hydrochloric Acid → Diethylammonium

HRID 2075205Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][C:17]=1[C:18]1[O:19][C:20]2[CH:26]=[CH:25][C:24]([CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=3)=[CH:23][C:21]=2[CH:22]=1)[CH2:5][N:6]1[CH2:9][CH:8]([C:10]([O:12]CC)=[O:11])[CH2:7]1.[Li+].[OH-].Cl>C1COCC1.O>[F:1][C:2]1[CH:3]=[C:4]([CH2:5][N:6]2[CH2:7][CH:8]([C:10]([OH:12])=[O:11])[CH2:9]2)[CH:15]=[CH:16][C:17]=1[C:18]1[O:19][C:20]2[CH:26]=[CH:25][C:24]([CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=3)=[CH:23][C:21]=2[CH:22]=1.[CH2:5]([NH2+:6][CH2:7][CH3:8])[CH3:4]

Participants

Conditions

Temperature: 24 °C

Procedure

A mixture of ethyl 1-(3-fluoro-4-(5-(pyridin-2-ylmethyl)benzofuran-2-yl)benzyl)azetidine-3-carboxylate (31 mg, 70 μmol) in THF (2 mL) was treated with 1M LiOH in H2O (0.4 mL) and stirred at 24° C. for 3 h, neutralized with 0.1M aqueous HCl, and evaporated. Purification by SFC (supercritical flash chromatography) resulted in title compound as its diethylammonium salt [hS1P1 EC50=31 nM]. 1H NMR (400 MHz, CD3OD) δ ppm 8.48 (d, J=0.8 Hz, 1H), 8.02 (t, J=7.9 Hz, 1H), 7.78 (t, J=5.9 Hz, 1H), 7.54 (s, 1H), 7.48 (d, J=10.0 Hz, 1H), 7.33-7.22 (m, 6H), 4.25 (s, 2H), 3.95 (s, 2H), 3.82 (t, J=8.6 Hz, 2H), 3.68 (t, J=8.5 Hz, 2H), 3.36-3.34 (m, 1H, partially overlapping with CD3OH signal), 3.05 (q, J=7.4 Hz, 2H), 1.31 (t, J=7.2 Hz, 3H). MS (ESI) m/z: Calculated: 416.2; Observed: 417.2 (M++1).

Workup

customevaporated
customPurification by SFC (supercritical flash chromatography)

Sources & evidence

ORD record: ord-96fc8f8059d146f6b521f3c123a0c536
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07919519B2

Reaction notes

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