Sodium Bicarbonate → HCID 66743691, compound

HRID 2363941Notes

Reaction equation

[NH2:1][C:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=2)[S:4][C:3]=1[C:13]([NH2:15])=[O:14].[C:16]([N:23]1[CH2:28][CH2:27][C:26](=O)[CH2:25][CH2:24]1)([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])O.[Na+]>C(O)(=O)C>[O:14]=[C:13]1[NH:15][C:26]2([CH2:27][CH2:28][N:23]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:24][CH2:25]2)[NH:1][C:2]2[CH:6]=[C:5]([C:7]3[CH:8]=[CH:9][N:10]=[CH:11][CH:12]=3)[S:4][C:3]1=2

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 3-amino-5-(pyridin-4-yl)thiophene-2-carboxamide (0.108 g, 0.500 mmol), N-Boc-piperidin-4-one (0.600 mg, 3.00 mmol), p-toluenesulfonic acid monohydrate (0.0095 g, 0.050 mmol) and acetic acid (3.0 mL) was stirred for 1 h at 70° C. The mixture was poured into sat. aqueous sodium hydrogen carbonate (100 mL). Extraction with ethyl acetate-tetrahydrofuran (3:1, 100 mL), drying over magnesium sulfate, filtration and concentration at reduced pressure gave a solid. The solid was triturated with ethyl acetate-dichloromethane, and the precipitate was collected by filtration to afford the title compound (0.184 g, 92%) as a yellow solid:

Workup

extractionExtraction with ethyl acetate-tetrahydrofuran (3:1, 100 mL)
dry with materialdrying over magnesium sulfate, filtration and concentration at reduced pressure
customgave a solid
customThe solid was triturated with ethyl acetate-dichloromethane
filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record: ord-148d7be769034b37b25d5bdd4a8e079d
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691828B2

Reaction notes

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