Hydrogen Peroxide → HCID 178445775, compound

HRID 2404140Notes

Reaction equation

[C:1]([C@H:5]1[CH2:10][CH2:9][C@H:8]([O:11][C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[CH:18]=[C:17]([CH2:22][NH:23][CH2:24][CH2:25][C:26]#[N:27])[CH:16]=[CH:15]3)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=[O:29].[K+].[K+].OO>CS(C)=O>[C:1]([C@H:5]1[CH2:10][CH2:9][C@H:8]([O:11][C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[CH:18]=[C:17]([CH2:22][NH:23][CH2:24][CH2:25][C:26]([NH2:27])=[O:29])[CH:16]=[CH:15]3)[CH2:7][CH2:6]1)([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 3-((6-((trans)-4-tert-butylcyclohexyloxy)naphthalen-2-yl)methylamino)propanenitrile (233 mg, 0.64 mmol) in DMSO (2 mL) was added K2CO3 (265 mg, 2 mmol, 3.0 eq), the mixture was then cooled to 0° C., and followed by addition of aq. 30% H2O2 (0.3 mL). The reaction mixture was stirred at rt for 1 h, and quenched with water (10 mL). The solvent was removed by freeze n-dried. The crude product was purified by flash chromatography to give the title compound as a white solid (111 mg, 45%) (mobile phase: MeOH/H2O: 0%˜80%). ESI-MS (M+1)+: 383.3. HPLC: 97.84%. 1H NMR (400 MHz, CD3OD) δ: 7.86˜7.79 (m, 3H), 7.53˜7.50 (m, 1H), 7.33˜7.30 (m, 1H), 7.21˜7.16 (m, 1H), 4.42˜4.35 (m, 3H), 3.34˜3.27 (m, 2H), 2.71 (t, 2H), 2.32˜2.24 (m, 2H), 1.96˜1.87 (m, 2H), 1.51˜1.39 (m, 2H), 1.33˜1.20 (m, 2H), 1.17˜1.09 (m, 1H), 0.92 (s, 9H).

Workup

customquenched with water (10 mL)
customThe solvent was removed by freeze n-dried
customThe crude product was purified by flash chromatography

Sources & evidence

ORD record: ord-d8fbcd19c9bc48dfa72ceffee206dad4
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08802659B2

Reaction notes

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