1-(4-(6-(4-Methoxybenzylamino)pyrimidin-4-yloxy)-3-fluorophenyl)-3-(2-(4-fluorophenyl)acetyl)urea → HCID 59301602, compound

HRID 1670259Notes

Reaction equation

HRID 1670259 reaction equation
[NH2:1][C:2]1[CH:30]=[CH:29][C:5]([O:6][C:7]2[CH:12]=[CH:11][N:10]=[CH:9][C:8]=2[C:13]#[C:14][CH2:15][N:16]2[CH2:19][CH:18]([CH2:20][NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:17]2)=[C:4]([F:31])[CH:3]=1.[CH3:32][O:33][C:34]1[CH:69]=[CH:68][C:37]([CH2:38][NH:39][C:40]2[N:45]=[CH:44][N:43]=[C:42]([O:46][C:47]3[CH:52]=[CH:51][C:50]([NH:53][C:54]([NH:56][C:57](=[O:66])[CH2:58][C:59]4[CH:64]=[CH:63][C:62]([F:65])=[CH:61][CH:60]=4)=[O:55])=[CH:49][C:48]=3[F:67])[CH:41]=2)=[CH:36][CH:35]=1>>[F:65][C:62]1[CH:61]=[CH:60][C:59]([CH2:58][C:57]([N:56]=[C:54]=[O:55])=[O:66])=[CH:64][CH:63]=1.[CH3:32][O:33][C:34]1[CH:35]=[CH:36][C:37]([CH2:38][NH:39][C:40]2[N:45]=[CH:44][N:43]=[C:42]([O:46][C:47]3[CH:52]=[CH:51][C:50]([NH:53][C:54]([NH:56][C:57](=[O:66])[CH2:58][C:59]4[CH:64]=[CH:63][C:62]([F:65])=[CH:61][CH:60]=4)=[O:55])=[CH:49][C:48]=3[F:67])[CH:41]=2)=[CH:68][CH:69]=1.[F:31][C:4]1[CH:3]=[C:2]([NH:1][C:54]([NH:56][C:57](=[O:66])[CH2:58][C:59]2[CH:64]=[CH:63][C:62]([F:65])=[CH:61][CH:60]=2)=[O:55])[CH:30]=[CH:29][C:5]=1[O:6][C:7]1[CH:12]=[CH:11][N:10]=[CH:9][C:8]=1[C:13]#[C:14][CH2:15][N:16]1[CH2:17][CH:18]([CH2:20][NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:19]1

Participants

5

Reactant 2

HCID 115698931-(4-(6-(4-Methoxybenzylamino)pyrimidin-4-yloxy)-3-fluorophenyl)-3-(2-(4-fluorophenyl)acetyl)ureaHCID 59853022HCID 59853022, compound

Product 3

HCID 115698931-(4-(6-(4-Methoxybenzylamino)pyrimidin-4-yloxy)-3-fluorophenyl)-3-(2-(4-fluorophenyl)acetyl)ureaHCID 231530882-(4-Fluorophenyl)acetyl isocyanateHCID 59301602HCID 59301602, compoundYield 57%

Procedure

The title compound was prepared from tert-butyl (1-(3-(4-(4-amino-2-fluorophenoxy)pyridin-3-yl)prop-2-ynyl)azetidin-3-yl)methylcarbamate (25 mg, 0.059 mmol) and a 0.3 M solution of 2-(4-fluorophenyl)acetyl isocyanate in toluene (Compound D of Example 11, 0.37 mL, 0.11 mmol) in the same manner as Step D of Example 33 to give the title compound as a white solid (20 mg, 57%). 1H NMR (DMSO-d6) δ 11.04 (s, 1H), 10.58 (s, 1H), 8.63 (s, 1H), 8.37 (d, 1H, J=5.5 Hz), 7.78 (d, 1H, J=12.6 Hz), 7.40-7.33 (m, 4H), 7.16 (dd, 2H, J=8.8, 8.9 Hz), 6.89-6.87 (m, 1H), 6.68 (d, 1H, J=5.5 Hz), 3.73 (s, 2H), 3.45 (s, 2H), 3.26-3.24 (m, 2H), 3.07-3.04 (m, 2H), 2.98-2.96 (m, 2H), 2.38-2.35 (m, 2H), 1.32 (s, 9H); MS (ESI+): m/z 606.26 (M+H)+.

Sources & evidence

ORD record
ord-1fb4856ea4964071839c972175a879c7
Source dataset
uspto-grants-2011_08
Patent number
US07989477B2

Reaction notes

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