N-[4-(2-Amino-4-methyl-phenylsulfanyl)-phenyl]-acetamide → N-[4-[4-methyl-2-[(7-propylpyrido[2,3-d]pyrimidin-4-yl)amino]phenyl]sulfanylphenyl]acetamide

HRID 607239Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[S:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:19])[CH3:18])=[CH:12][CH:11]=1.C([C:22]1[C:23]([N:31]=[CH:32][N:33]([CH3:35])C)=[N:24][C:25]([CH2:28][CH2:29][CH3:30])=[CH:26][CH:27]=1)#N>C(O)(=O)C>[CH3:8][C:6]1[CH:5]=[CH:4][C:3]([S:9][C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:19])[CH3:18])=[CH:12][CH:11]=2)=[C:2]([NH:1][C:35]2[C:22]3[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][CH3:30])=[N:24][C:23]=3[N:31]=[CH:32][N:33]=2)[CH:7]=1

Participants

Conditions

Temperature: 130 °C

Procedure

The product from Example 7b (49 mg 0.231 mmol) and the product from Example 128A (50 mg, 0.231 mmol) were dissolved in acetic acid (1 mL) and heated to 130° C. for 1.5 hours. After cooling to room temperature and removal of the acetic acid solvent under vacuum methanol (3 mL) was added to the oil which caused a solid to form which was triturated with methanol to provide the title compound 80 mg, 78%). 1H NMR (300 MHz, DMSO-D6) δ ppm: 0.95 (t, J=7.4 Hz, 3H), 1.89 (m, 2H), 2.02 (s, 3H), 2.32 (s, 3H), 2.89 (t, J=7.5 Hz, 2H), 7.06 (s, 2H), 7.21 (t, J=8.5 Hz, 2H), 7.30 (s, 1H), 7.50 (d, J=8.8 Hz, 2H), 7.52 (m, 1H), 8.52 (s, 1H), 8.74 (d, J=7.7 Hz, 1H), 10.00 (s, 1H); MS (ESI)+ m/z 444 (M+H)+.

Workup

temperatureAfter cooling to room temperature
customremoval of the acetic acid solvent under vacuum methanol (3 mL)
additionwas added to the oil which
customto form which
customwas triturated with methanol

Sources & evidence

ORD record: ord-80392b3139374ea68dbbd0dba9c93980
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07915411B2

Reaction notes

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