Sodium Hydroxide → HCID 44128909, compound

HRID 1514275Notes

Reaction equation

[C:1]([C:3]1[CH:4]=[C:5]([C:13]2[O:17][N:16]=[C:15]([C:18]3[CH:34]=[CH:33][C:21]4[CH2:22][CH2:23][N:24]([CH2:27][C:28]([O:30]CC)=[O:29])[CH2:25][CH2:26][C:20]=4[CH:19]=3)[N:14]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH:10]([CH3:12])[CH3:11])#[N:2].[OH-].[Na+]>C(O)C>[C:1]([C:3]1[CH:4]=[C:5]([C:13]2[O:17][N:16]=[C:15]([C:18]3[CH:34]=[CH:33][C:21]4[CH2:22][CH2:23][N:24]([CH2:27][C:28]([OH:30])=[O:29])[CH2:25][CH2:26][C:20]=4[CH:19]=3)[N:14]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH:10]([CH3:12])[CH3:11])#[N:2]

Participants

Conditions

Temperature: 40 °C

Procedure

A mixture of ethyl [7-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl]acetate (Preparation 47) (43 mg, 0.09 mmol), aqueous sodium hydroxide (2M, 430 μL, 0.86 mmol) and ethanol (4.3 ml) was heated at 40° C. for 1 h. The reaction mixture was cooled to room temperature and concentrated. The residue was taken up in water, which was then acidified to pH 6 with acetic acid. The aqueous phase was extracted with EtOAc (2×20 ml) and the combined organic fractions concentrated to give a white solid, which was then triturated with EtOAc to give the title compound as a white solid (36 mg, 0.08 mmol). δH (d6DMSO, 400 MHz): 8.50 (1H, d), 8.41 (1H, dd), 7.85-7.80 (2H, m), 7.55 (1H, d), 7.32 (1H, d), 4.98 (1H, septet), 3.00-2.91 (6H, m), 2.75-2.66 (4H, m), 1.39 (6H, d); MS (ES−): C24H24N4O4 requires 432; found 431 [M−H]+.

Workup

temperatureThe reaction mixture was cooled to room temperature
concentrationconcentrated
extractionThe aqueous phase was extracted with EtOAc (2×20 ml)
concentrationthe combined organic fractions concentrated
customto give a white solid, which
customwas then triturated with EtOAc

Sources & evidence

ORD record: ord-c9ceacde78f4410eb747b12432c16ae0
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08222245B2

Reaction notes

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