Potassium Hydroxide → HCID 25271116, compound

HRID 889732Notes

Reaction equation

C([O:3][C:4](=[O:42])[CH:5]([C:10]1[CH:11]=[C:12]([C:32]2[CH:37]=[CH:36][C:35]([C:38]([F:41])([F:40])[F:39])=[CH:34][CH:33]=2)[CH:13]=[C:14]([CH:16]2[CH2:21][CH2:20][CH2:19][N:18]([CH2:22][C:23]3[CH:31]=[CH:30][C:26]4[N:27]=[N:28][S:29][C:25]=4[CH:24]=3)[CH2:17]2)[CH:15]=1)[CH2:6][CH:7]([CH3:9])[CH3:8])C.[OH-].[K+]>CCO>[S:29]1[C:25]2[CH:24]=[C:23]([CH2:22][N:18]3[CH2:19][CH2:20][CH2:21][CH:16]([C:14]4[CH:15]=[C:10]([CH:5]([CH2:6][CH:7]([CH3:9])[CH3:8])[C:4]([OH:42])=[O:3])[CH:11]=[C:12]([C:32]5[CH:37]=[CH:36][C:35]([C:38]([F:40])([F:41])[F:39])=[CH:34][CH:33]=5)[CH:13]=4)[CH2:17]3)[CH:31]=[CH:30][C:26]=2[N:27]=[N:28]1

Participants

Conditions

Temperature: 78 °C

Procedure

To compound 49a, 2-[5-(1-Benzo[1,2,3]thiadiazol-6-ylmethyl-piperidin-3-yl)-4′-trifluoromethyl-biphenyl-3-yl]-4-methyl-pentanoic acid ethyl ester (67.0 mg, 0.11 mmol) in EtOH (5.0 ml) was added 2M KOH (0.56 ml, 1.1 mmol). The reaction was heated to 78° C. for 3 hour, cooled to room temperature, and concentrated in vacuo. Purification via Gilson HPLC, salt exchange with 1N HCl (aqueous) gave the product as a white lyophilate, (46 mg, 68%). 1H NMR (400 MHz, MeOD) δ ppm 0.89-0.96 (m, 6 H) 1.44-1.55 (m, 1 H) 1.63-1.71 (m, 1 H) 1.92-2.04 (m, 3 H) 2.13 (s, 2 H) 3.12-3/23 (m, 2 H) 3.32-3.39 (m, 1 H) 3.60-3.67 (m, 2 H) 3.76 (t, J=7.83 Hz, 1 H) 4.62-4.71 (m, 2 H) 7.33 (s, 1 H) 7.51 (s, 1 H) 7.57 (s, 1 H) 7.73-7.82 (m, 4 H) 7.90-7.96 (m, 1 H) 8.40 (d, J=8.31 Hz, 1 H) 8.87 (s, 1 H) Calcd for C31H32F3N3O2S (M+H) 567.67, Found 568.3.

Workup

temperaturecooled to room temperature
concentrationconcentrated in vacuo
customPurification via Gilson HPLC, salt exchange with 1N HCl (aqueous)
customgave the product as a white lyophilate, (46 mg, 68%)

Sources & evidence

ORD record: ord-e18e365da8724541a099cc4afebe023e
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08252935B2

Reaction notes

Loading…