1-(4-(6-Chloropyrimidin-4-yloxy)-3-fluorophenyl)-3-(2-(4-fluorophenyl)acetyl)thiourea → 1-(2-(4-Fluorophenyl)acetyl)-3-(4-(pyridin-4-yloxy)phenyl)thiourea

HRID 1670189Notes

Reaction equation

HRID 1670189 reaction equation
F[C:2]1C=CC(N(C2C=CC(OC3C=CN=CC=3)=CC=2)C(=O)CC(N)=O)=CC=1.Cl[C:29]1[N:34]=[CH:33]N=[C:31]([O:35][C:36]2[CH:41]=[CH:40][C:39]([NH:42][C:43]([NH:45][C:46](=[O:55])[CH2:47][C:48]3[CH:53]=[CH:52][C:51]([F:54])=[CH:50][CH:49]=3)=[S:44])=[CH:38][C:37]=2F)[CH:30]=1>>[F:54][C:51]1[CH:52]=[CH:53][C:48]([CH2:47][C:46]([NH:45][C:43]([NH:42][C:39]2[CH:40]=[CH:41][C:36]([O:35][C:31]3[CH:2]=[CH:33][N:34]=[CH:29][CH:30]=3)=[CH:37][CH:38]=2)=[S:44])=[O:55])=[CH:49][CH:50]=1

Participants

3

Reactant 2

HCID 115538441-(4-(6-Chloropyrimidin-4-yloxy)-3-fluorophenyl)-3-(2-(4-fluorophenyl)acetyl)thioureaHCID 11610278N-(4-Fluorophenyl)-N-(4-(pyridin-4-yloxy)phenyl)malonamide2×

Product 1

HCID 116680461-(2-(4-Fluorophenyl)acetyl)-3-(4-(pyridin-4-yloxy)phenyl)thioureaYield 10%

Procedure

The title compound was prepared using 4-(4-aminophenoxy)pyridine (Compound A of Example 1) and a similar procedure outlined for the preparation of Compound C of Example 2. Yield: 10%. 1H NMR (CDCl3) δ 12.3 (s, 1H), 8.63 (s, 1H), 8.49, (d, 2H, J=6.2 Hz), 7.71 (d, 2H, J=8.9 Hz), 7.31-7.27 (m, 2H), 7.14-7.09 (m, 4H), 6.90 (dd, 2H, J=4.8, 1.4 Hz), 3.73 (s, 2H); MS (ESI+) m/z 382.2 (M+H)+.

Sources & evidence

ORD record
ord-523a1f35c6034581a68c643a68a932a7
Source dataset
uspto-grants-2011_08
Patent number
US07989477B2

Reaction notes

Loading…