2-Aminothiazole → {4-[3-Isopropoxy-5-(thiazol-2-ylcarbamoyl)-phenoxy]-phenyl}-phosphonic acid diisopropyl ester
Reaction equation
[CH:1]([O:4][P:5]([C:11]1[CH:30]=[CH:29][C:14]([O:15][C:16]2[CH:17]=[C:18]([CH:22]=[C:23]([O:25][CH:26]([CH3:28])[CH3:27])[CH:24]=2)[C:19](O)=[O:20])=[CH:13][CH:12]=1)([O:7][CH:8]([CH3:10])[CH3:9])=[O:6])([CH3:3])[CH3:2].[NH2:31][C:32]1[S:33][CH:34]=[CH:35][N:36]=1.C(OC1C=C(C=C(C(=O)NC2SC=CN=2)C=1)OC1C=CC(P(=O)(O)O)=CC=1)(C)C>>[CH:8]([O:7][P:5]([C:11]1[CH:12]=[CH:13][C:14]([O:15][C:16]2[CH:17]=[C:18]([C:19](=[O:20])[NH:31][C:32]3[S:33][CH:34]=[CH:35][N:36]=3)[CH:22]=[C:23]([O:25][CH:26]([CH3:27])[CH3:28])[CH:24]=2)=[CH:29][CH:30]=1)(=[O:6])[O:4][CH:1]([CH3:2])[CH3:3])([CH3:10])[CH3:9]Participants
4
Reactant 3
Product 1
Procedure
Starting from 3-[4-(diisopropoxy-phosphoryl)-phenoxy]-5-isopropoxy-benzoic acid (7.64 g, 17.6 mmol) and 2-aminothiazole (1.84 g, 18.4 mmol), {4-[3-isopropoxy-5-(thiazol-2-ylcarbamoyl)-phenoxy]-phenyl}-phosphonic acid was synthesized as yellow gum (8.80 g, 17.0 mmol) according to Step D in Example 1. 1H NMR (300 MHz, CDCl3): δ 7.78 (dd, J=9, 13 Hz, 2H), 7.29-7.30 (m, 1H), 7.18-7.20 (m, 2H), 7.04 (dd, J=4, 9 Hz, 2H), 6.94 (d J=4 Hz, 1H), 6.78 (dd, J=2, 2 Hz, 1H), 4.63-4.74 (m, 2H), 4.51-4.59 (m, 1H), 1.36 (d, J=6 Hz, 6H), 1.33 (d, J=6 Hz, 6H) 1.24 (d, J=6 Hz, 6H).
Sources & evidence
- ORD record
- ord-5f7f797ebb0e4e10932fff307072da69
- Source dataset
- uspto-grants-2015_01
- Patent number
- US08940927B2
Reaction notes
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