Hydrochloric Acid → HCID 59471935, compound

HRID 2204863Notes

Reaction equation

C([O:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[O:13][C:14]([C:17]3[C:22]([NH2:23])=[N:21][CH:20]=[C:19]([C:24]4[CH:29]=[CH:28][C:27]([C:30](=[O:34])[N:31]([CH3:33])[CH3:32])=[CH:26][CH:25]=4)[N:18]=3)=[N:15][N:16]=2)=[CH:8][CH:7]=1)(=O)C.[OH-].[Na+].Cl>CO>[NH2:23][C:22]1[N:21]=[CH:20][C:19]([C:24]2[CH:29]=[CH:28][C:27]([C:30]([N:31]([CH3:33])[CH3:32])=[O:34])=[CH:26][CH:25]=2)=[N:18][C:17]=1[C:14]1[O:13][C:12]([C:9]2[CH:8]=[CH:7][C:6]([CH2:5][OH:4])=[CH:11][CH:10]=2)=[N:16][N:15]=1

Participants

Conditions

Temperature: 55 °C

Procedure

[4-[5-[3-amino-6-[4-(dimethylcarbamoyl)phenyl]pyrazin-2-yl]-1,3,4-oxadiazol-2-yl]phenyl]methyl acetate (118 mg, 0.2445 mmol) was suspended in methanol (2 mL) and treated with NaOH (489.0 μL of 1 M, 0.4890 mmol). The resulting mixture was stirred at 55° C. for 1 h. The reaction mixture was cooled to room temperature and then neutralised with HCl (978.0 μL of 1 M, 0.9780 mmol), filtered and washed with acetonitrile. The resulting yellow powder was heated in acetonitrile (5 mL), cooled and filtered to give a pale yellow powder. This was purified by column chromatography on silica gel eluting with 5% MeOH/CH2Cl2 to give the product as a pale yellow powder (73 mg, 70%); 1H NMR (400 MHz, DMSO) d 2.98-3.02 (m, 6H), 4.64 (d, 2H), 5.44 (t, 1H), 7.54-7.62 (dd, 4H), 7.78 (br s, 2H), 8.12-8.18 (dd, 4H) and 8.98 (s, 1H) ppm; MS (ES+) 417.23

Workup

temperatureThe reaction mixture was cooled to room temperature
filtrationfiltered
washwashed with acetonitrile
temperatureThe resulting yellow powder was heated in acetonitrile (5 mL)
temperaturecooled
filtrationfiltered
customto give a pale yellow powder
customThis was purified by column chromatography on silica gel eluting with 5% MeOH/CH2Cl2

Sources & evidence

ORD record: ord-9177d2ddc48a44b9adb500a7e39309db
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09365557B2

Reaction notes

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