Hydrochloric Acid → HCID 68683347, compound

HRID 1713743Notes

Reaction equation

[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=1[NH:10][C:11]1[O:15][C:14]([C:16]([NH:18][C:19]2[CH:20]=[CH:21][C:22]([N:25]3[CH2:30][CH2:29][CH:28]([CH2:31][C:32]([O:34]C)=[O:33])[CH2:27][CH2:26]3)=[N:23][CH:24]=2)=[O:17])=[N:13][N:12]=1.[OH-].[Li+].[ClH:38]>CO.C1COCC1>[ClH:38].[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=1[NH:10][C:11]1[O:15][C:14]([C:16]([NH:18][C:19]2[CH:20]=[CH:21][C:22]([N:25]3[CH2:26][CH2:27][CH:28]([CH2:31][C:32]([OH:34])=[O:33])[CH2:29][CH2:30]3)=[N:23][CH:24]=2)=[O:17])=[N:13][N:12]=1

Participants

Conditions

Temperature: 45 °C

Procedure

Methyl (1-{5-[({5-[(2,4,5-trifluorophenyl)amino]-1,3,4-oxadiazol-2-yl}carbonyl)-amino]pyridin-2-yl}piperidin-4-yl)acetate (Example 319, 216 mg, 0.44 mmol) was suspended in a mixture of MeOH (4 ml) and THF (8 mL). Lithium hydroxide (4.4 mL of a 1M aqueous solution) was added. The resulting clear solution was heated at 45° C. for 15 minutes then cooled and acidified to pH ˜2 with dropwise addition of concentrated aqueous HCl. Volatile material was removed by evaporation and the residue was washed with water then dried to give the title compound (182 mg, 87%) as a solid; 1H NMR δ 1.16-1.45 (2H, m), 1.76-1.93 (2H, m), 1.98-2.13 (1H, m), 2.28 (2H, d), 3.12 (2H, t), 4.28 (2H, d), 7.25-7.41 (1H, m), 7.70-7.88 (1H, m), 8.13-8.32 (2H, m), 8.55 (1H, d), 11.16 (1H, s), 11.29 (1H, s); MS m/e MH+ 477.

Workup

temperaturethen cooled
customVolatile material was removed by evaporation
washthe residue was washed with water
customthen dried

Sources & evidence

ORD record: ord-b2adc9827a9a49e8948bdb84a8ce91a1
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07795283B2

Reaction notes

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