p-Toluenesulfonic acid → HCID 117775245, compound

HRID 2201550Notes

Reaction equation

[NH2:1][C:2]1[N:10]=[CH:9][C:8]([Br:11])=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].[S:12]1[CH:16]=[CH:15][CH:14]=[C:13]1[CH:17]=O.CC1C=CC(S(O)(=O)=O)=CC=1>CO>[Br:11][C:8]1[CH:9]=[N:10][C:2]2[NH:1][CH:17]([C:13]3[S:12][CH:16]=[CH:15][CH:14]=3)[NH:6][C:4](=[O:5])[C:3]=2[CH:7]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a mixture of 2-amino-5-bromonicotinamide (200 mg, 0.93 mmol), thiophene-2-carbaldehyde (125 mg, 1.11 mmol) in MeOH (15 mL) was added 4-methylbenzenesulfonic acid (16 mg, 0.09 mmol). The mixture was stirred at 60° C. overnight. Then the resulting solid was filtered to give the product of 6-bromo-2-(thiophen-2-yl)-2,3-dihydropyrido[2,3-d]pyrimidin-4(1H)-one (180 mg, yield: 63%), which was used for the next step without further purification. 1H NMR (DMSO-d6, 400 MHz) δ 8.93 (d, J=2.4 Hz, 1H), 8.42 (s, 1H), 8.28 (d, J=2.4 Hz, 1H), 7.98 (d, J=2.4 Hz, 1H), 7.45 (dd, J=4.8 Hz, 1.2 Hz, 1H), 7.08 (d, J=3.2 Hz, 1H), 6.98 (dd, J=4.8 Hz, 3.2 Hz, 1H), 6.10 (t, J=2.4 Hz, 1H). MS (M+H)+: 310/312.

Workup

filtrationThen the resulting solid was filtered

Sources & evidence

ORD record: ord-5351c68a7e8b482fad9caa3b9fbffff2
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09364482B2

Reaction notes

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