HCID 68302560, compound → HCID 52938418, compound

HRID 1807587Notes

Reaction equation

[C:1]([C:3]1[CH:4]=[C:5]([C:13]2[O:17][N:16]=[C:15]([C:18]3[CH:27]=[CH:26][CH:25]=[C:24]4[C:19]=3[CH2:20][CH2:21][CH2:22][C@H:23]4[N:28]([CH2:36][CH2:37][OH:38])C(=O)OC(C)(C)C)[N:14]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH:10]([CH3:12])[CH3:11])#[N:2]>O1CCOCC1>[OH:38][CH2:37][CH2:36][NH:28][C@@H:23]1[CH2:22][CH2:21][CH2:20][C:19]2[C:18]([C:15]3[N:14]=[C:13]([C:5]4[CH:6]=[CH:7][C:8]([O:9][CH:10]([CH3:12])[CH3:11])=[C:3]([CH:4]=4)[C:1]#[N:2])[O:17][N:16]=3)=[CH:27][CH:26]=[CH:25][C:24]1=2

Participants

Conditions

Temperature: 50 °C

Procedure

Prepared using General Procedure 11. To a stirred solution of (R)-tert-butyl (5-(5-(3-cyano-4-isopropoxyphenyl)-1,2,4-oxadiazol-3-yl)-1,2,3,4-tetrahydronaphthalen-1-yl)(2-hydroxyethyl)carbamate INT-23 (15 mg, 0.03 mmol) in dioxane (1 mL) was added 4N HCl/dioxanes (116 μL, 0.116 mmol). After heating at 50° C. for 18 h, the mixture was concentrated and the resulting solid was purified by preparative HPLC to provide 9.53 mg (79%) of (R)-5-(3-(5-((2-hydroxyethyl)amino)-5,6,7,8-tetrahydronaphthalen-1-yl)-1,2,4-oxadiazol-5-yl)-2-isopropoxy benzonitrile 50. LCMS-ESI (m/z) calculated for C24H26N4O3: 418.5; found 419.2 [M+H]+, tR=2.52 min. 1H NMR (400 MHz, CDCl3) δ 8.39 (d, J=2.2 Hz, 1H), 8.32 (dd, J=8.9, 2.2 Hz, 1H), 8.04 (d, J=7.7 Hz, 1H), 7.60 (d, J=7.6 Hz, 1H), 7.39 (t, J=7.7 Hz, 1H), 7.12 (d, J=9.1 Hz, 1H), 4.88-4.70 (m, 1H), 4.54 (s, 1H), 3.78 (d, J=12.1 Hz, 2H), 3.62 (s, 2H), 3.24 (dt, J=18.0, 5.6 Hz, 1H), 3.18-2.89 (m, 3H), 2.16 (d, J=5.2 Hz, 2H), 2.10-1.75 (m, 2H), 1.47 (d, J=6.1 Hz, 6H).

Workup

customPrepared
concentrationthe mixture was concentrated
customthe resulting solid was purified by preparative HPLC

Sources & evidence

ORD record: ord-a9a557d57630477eb3a23387f700be98
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08357706B2

Reaction notes

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