3-Cyclopropyl-3-Oxopropionic Acid Methyl Ester → HCID 67072254, compound

HRID 1242437Notes

Reaction equation

HRID 1242437 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[C:5]([O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][C:10]=1[CH3:16])([CH3:7])[CH3:6])[CH3:2].Cl[CH2:19][C:20]1[C:21]([CH:36]2[CH2:38][CH2:37]2)=[N:22][C:23]([C:26]2[CH:27]=[N:28][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:30][CH:31]=2)=[N:24][CH:25]=1.C1(C(=O)CC(OC)=O)CC1.Cl.FC(F)(F)C1C=CC(C(N)=N)=CC=1>>[CH2:1]([O:3][C:4](=[O:17])[C:5]([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:19][C:20]2[C:21]([CH:36]3[CH2:38][CH2:37]3)=[N:22][C:23]([C:26]3[CH:27]=[N:28][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:30][CH:31]=3)=[N:24][CH:25]=2)=[CH:11][C:10]=1[CH3:16])([CH3:6])[CH3:7])[CH3:2]

Participants

5

Reactant 4

HCID 101300163-Cyclopropyl-3-Oxopropionic Acid Methyl EsterHCID 125357914-(Trifluoromethyl)benzamidine HydrochlorideHCID 16756990Ethyl 2-(4-hydroxy-2-methylphenoxy)-2-methylpropanoateHCID 21935911HCID 21935911, compound

Product 1

HCID 67072254HCID 67072254, compound

Procedure

In analogy to the procedures described in example 101A], 2-(4-hydroxy-2-methyl-phenoxy)-2-methyl-propionic acid ethyl ester (described in WO 02/092590) was reacted with 5-chloromethyl-4-cyclopropyl-2-(6-trifluoromethyl-pyridin-3-yl)-pyrimidine (prepared from methyl 3-cyclopropyl-3-oxopropanoate and 4-(trifluoromethyl)benzamidine hydrochloride, in analogy to the procedures described in examples 101C] to 101F]) to give 2-{4-[4-cyclopropyl-2-(6-trifluoromethyl-pyridin-3-yl)-pyrimidin-5-ylmethoxy]-2-methyl-phenoxy}-2-methyl-propionic acid ethyl ester, which was subsequently saponified in analogy to the procedure described in example 101B] to yield the title compound as off-white crystalls of mp. 185.0–185.5° C.

Sources & evidence

ORD record
ord-e448a4c2592f4c77a6bfcd3b1ddc9acd
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

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