HCID 67387134, compound → HCID 53390116, compound

HRID 2408849Notes

Reaction equation

[O:1]=[C:2]1[C:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH2:5][CH2:4][N:3]1[CH2:19][C:20]([N:22]1[CH2:27][CH2:26][N:25](C(OCC2C=CC=CC=2)=O)[CH2:24][CH2:23]1)=[O:21]>O1CCCC1>[O:21]=[C:20]([N:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1)[CH2:19][N:3]1[CH2:4][CH2:5][C:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:2]1=[O:1]

Participants

Conditions

Temperature: 50 °C

Procedure

A 50 mL pressure bottle was charged with tetrahydrofuran (10 mL), the product from Example 24A (0.450 g, 0.904 mmol) and 20% Pd(OH)2—C, wet (0.090 g, 0.641 mmol). The reaction mixture was stirred at 50° C. under an atmosphere of 30 psi H2 for 15 minutes. The mixture was filtered through a nylon membrane and concentrated in vacuo. The crude product was purified by chromatography on silica gel (Analogix Intelliflash 280; 2N NH4OH in CH3OH/CH2Cl2, 2:98, eluant) to afford the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 7.36-7.19 (m, 10H), 4.16 (s, 2H), 3.40-3.25 (m, 7H), 2.73 (t, J=6.5, 2H), 2.68-2.59 (m, 4H); MS (DCI+) m/z 364 (M+H)+.

Workup

filtrationThe mixture was filtered through a nylon membrane
concentrationconcentrated in vacuo
customThe crude product was purified by chromatography on silica gel (Analogix Intelliflash 280; 2N NH4OH in CH3OH/CH2Cl2, 2:98, eluant)

Sources & evidence

ORD record: ord-77a03673fbcc407481fd54447a72f197
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815869B2

Reaction notes

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