p-Toluenesulfonic acid → HCID 11628653, compound

HRID 1038735Notes

Reaction equation

Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([N:8]([CH3:32])[C:9](=[O:31])[NH:10][C:11]2[CH:12]=[C:13]([NH:18][C:19](=[O:30])[C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=3)[CH:14]=[CH:15][C:16]=2[CH3:17])[CH:3]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[N:44]1([C:50]2[CH:55]=[CH:54][C:53]([NH2:56])=[CH:52][CH:51]=2)[CH2:49][CH2:48][O:47][CH2:46][CH2:45]1>CN(C=O)C>[CH3:17][C:16]1[CH:15]=[CH:14][C:13]([NH:18][C:19](=[O:30])[C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=2)=[CH:12][C:11]=1[NH:10][C:9]([N:8]([CH3:32])[C:4]1[CH:3]=[C:2]([NH:56][C:53]2[CH:52]=[CH:51][C:50]([N:44]3[CH2:49][CH2:48][O:47][CH2:46][CH2:45]3)=[CH:55][CH:54]=2)[N:7]=[CH:6][N:5]=1)=[O:31]

Participants

Conditions

Temperature: 80 °C

Procedure

N-{3-[3-(6-Chloro-pyrimidin-4-yl)-3-methyl-ureido]-4-methyl-phenyl}-3-trifluoromethyl-benzamide (50 mg, 0.107 mmol) and p-toluenesulfonic acid (20 mg, 0.105 mmol) were mixed and dissolved in 1 ml DMF. Then 4-Morpholin-4-yl-phenylamine (22 mg, 0.11 mmol) was added to it. The reaction was stirred at 80° C. for 10 hours. The crude product was purified by reverse phase HPLC to give final product N-(4-Methyl-3-{3-methyl-3-[6-(4-morpholin-4-yl-phenylamino)-pyrimidin-4-yl]-ureido}-phenyl)-3-trifluoromethyl-benzamide as grey solid, 48 mg; 1H NMR 600 MHz (DMSO) δ 12.74 (s, 1H), 10.46 (s, 1H), 9.53 (s, 1H), 8.47 (s, 1H), 8.41 (m, 1H), 8.31 (s, 1H), 8.28 (d, 1H, J=7.8 Hz), 7.97 (d, 1H, J=7.2 Hz), 7.79 (t, 1H, J=4.2 Hz), 7.52 (d, 1H, J=7.8 Hz), 7.47 (d, 2H, J=8.4 Hz), 7.22 (d, 1H, J=8.4 Hz), 6.99 (s, 1H), 6.98 (s, 1H), 6.34 (s, 1H), 4.15 (m, 4H), 3.76 (m, 4H), 3.10 (m, 3H), 2.32 (s, 3H); MS m/z 606.2 (M+1).

Workup

customThe crude product was purified by reverse phase HPLC

Sources & evidence

ORD record: ord-a2373796c43e41c9ba6e240d9311ae99
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08552002B2

Reaction notes

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