p-Toluenesulfonic acid → HCID 16042219, compound

HRID 252198Notes

Reaction equation

HRID 252198 reaction equation
[C:1]([NH:5][C:6](=[O:43])[NH:7][C:8]1[C:9]([C:22]2[C:23]([Cl:42])=[C:24]([NH:29][C:30](=[O:41])[C:31]3[CH:36]=[CH:35][CH:34]=[C:33]([C:37]([F:40])([F:39])[F:38])[CH:32]=3)[CH:25]=[CH:26][C:27]=2[Cl:28])=[CH:10][C:11]2[CH:16]=[N:15][C:14](S(C)(=O)=O)=[N:13][C:12]=2[N:21]=1)([CH3:4])([CH3:3])[CH3:2].C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:55]([N:57]([CH2:68][CH3:69])[CH2:58][CH2:59][O:60][C:61]1[CH:66]=[CH:65][C:64]([NH2:67])=[CH:63][CH:62]=1)[CH3:56]>CN(C=O)C>[C:1]([NH:5][C:6](=[O:43])[NH:7][C:8]1[C:9]([C:22]2[C:23]([Cl:42])=[C:24]([NH:29][C:30](=[O:41])[C:31]3[CH:36]=[CH:35][CH:34]=[C:33]([C:37]([F:40])([F:39])[F:38])[CH:32]=3)[CH:25]=[CH:26][C:27]=2[Cl:28])=[CH:10][C:11]2[CH:16]=[N:15][C:14]([NH:67][C:64]3[CH:63]=[CH:62][C:61]([O:60][CH2:59][CH2:58][N:57]([CH2:68][CH3:69])[CH2:55][CH3:56])=[CH:66][CH:65]=3)=[N:13][C:12]=2[N:21]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 4189324-(2-(Diethylamino)ethoxy)anilineHCID 59860295HCID 59860295, compound

Product 1

HCID 16042219HCID 16042219, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

This compound is prepared using a similar procedure to the one described above except that in step D the following procedure is used. To a solution of N—{3-[7-(3-tert-butyl-ureido)-2-methanesulfonyl-pyrido[2,3-d]pyrimidin-6-yl]-2,4-dichloro-phenyl}-3-trifluoromethyl-benzamide (50 mg, 0.08 mmol) in DMF (2 ml) is added p-toluenesulfonic acid (15 mg, 0.08 mmol) and 4-(2-diethylamino-ethoxy)-phenylamine (21 mg, 0.1 mmol). The reaction is stirred at 80° C. for 4 hours. The crude product is purified by RP-HPLC to give the title compound as yellow solid: 1H NMR 400 MHz (DMSO) δ 10.46 (s, 1H), 10.09 (s, 1H), 9.30 (s, 1H), 9.05 (s, 1H), 8.28 (s, 1H), 8.24 (d, 1H, J=7.6 Hz), 8.05 (m, 2H), 7.95 (m, 3H), 7.76 (m, 3H), 7.67 (d, 2H, J=8.8 Hz), 4.24 (t, 2H, J=4.6 Hz), 3.45 (m, 2H), 3.15 (m, 4H), 1.39 (s, 9H), 1.18 (t, 6H, J=7.2 Hz); MS m/z 783.3 (M+1).

Workup

  1. customThis compound is prepared
  2. customThe crude product is purified by RP-HPLC

Sources & evidence

ORD record
ord-b19cdf509a8b41b49d071f1db5208f33
Source dataset
uspto-grants-2011_01
Patent number
US07868018B2

Reaction notes

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