HCID 67248884, compound → HCID 67248740, compound

HRID 1035312Notes

Reaction equation

C([N:8]1[CH2:18][CH2:17][N:16]2[C@@H:10]([CH2:11][CH2:12][O:13][C:14]3[C:22]([CH3:23])=[CH:21][CH:20]=[CH:19][C:15]=32)[CH2:9]1)C1C=CC=CC=1>C(O)C(F)(F)F>[CH3:23][C:22]1[C:14]2[O:13][CH2:12][CH2:11][C@H:10]3[CH2:9][NH:8][CH2:18][CH2:17][N:16]3[C:15]=2[CH:19]=[CH:20][CH:21]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of Example 226B (923 mg, 2.99 mmol) in trifluoroethanol (20 mL) was added Pd(OH)2—C (20%, wet, 185 mg, 1.3 mmol). The reaction mixture was stirred under H2 (30 psi) at 50° C. for 90 minutes after which the mixture was filtered through a nylon membrane. The solution was concentrated and purified via flash chromatography (0-30% methanol/dichloromethane) to afford the title compound 1H NMR (300 MHz, DMSO-d6) δ ppm 6.67-6.85 (m, 3H), 4.22-4.39 (m, 1H), 4.04-4.18 (m, 1H), 2.55-3.03 (m, 7H), 2.09 (s, 3H), 1.80-1.95 (m, 1H); MS (ESI+) m/z 219 (M+H)+.

Workup

filtrationwas filtered through a nylon membrane
concentrationThe solution was concentrated
custompurified via flash chromatography (0-30% methanol/dichloromethane)

Sources & evidence

ORD record: ord-e78a03d247ea4e9b8826da2389c8dc20
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546377B2

Reaction notes

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