Ammonium → HCID 15950890, compound

HRID 252197Notes

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].[NH4+].CC[N:47](C(C)C)C(C)C>CO>[NH2:47][C:14]1[N:15]=[CH:16][C:11]2[CH:10]=[C:9]([C:22]3[C:23]([Cl:42])=[C:24]([NH:29][C:30](=[O:41])[C:31]4[CH:36]=[CH:35][CH:34]=[C:33]([C:37]([F:38])([F:39])[F:40])[CH:32]=4)[CH:25]=[CH:26][C:27]=3[Cl:28])[C:8]([NH:7][C:6]([NH:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:43])=[N:21][C:12]=2[N:13]=1

Participants

Conditions

Temperature: 80 °C

Procedure

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 (80 mg, 0.12 mmol) in methanol (5 ml) is added ammonium (methanol solution, 20 ml, 0.14 mmol) and DIEA (41 μl, 0.24 mmol). The reaction is stirred at 80° C. for 4 hours. The methanol is removed by rotary evaporation and the crude product is purified by RP-HPLC to give the title compound as a white solid: 1H NMR 400 MHz (DMSO) δ 10.46 (s, 1H), 8.93 (s, 1H), 8.27 (s, 1H), 8.23 (d, 2H, J=8.0 Hz), 8.00 (s, 1H), 7.96 (d, 1H, J=8.4 Hz), 7.76 (m, 3H), 7.68 (d, 1H, J=8.8 Hz), 7.48 (s, 2H), 1.32 (s, 9H); MS m/z 592.2 (M+1).

Workup

customThe methanol is removed by rotary evaporation
customthe crude product is purified by RP-HPLC

Sources & evidence

ORD record: ord-6369ad7be15947789fc9f033b3a493f6
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07868018B2

Reaction notes

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