Methyl 3-Hydroxyphenylacetate → HCID 69666999, compound

HRID 1242496Notes

Reaction equation

HRID 1242496 reaction equation
[CH:1]1([C:4]2[C:9]([NH2:10])=[CH:8][N:7]=[C:6]([C:11]3[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=3)[N:5]=2)[CH2:3][CH2:2]1.FC(F)(F)C1C(C(O)=O)=CN=C(C2C=CC(C(F)(F)F)=CC=2)N=1.[C:44]([O:48][C:49](=[O:64])[C:50]([O:53][C:54]1[CH:59]=[CH:58][CH:57]=[C:56]([CH2:60][C:61](O)=[O:62])[CH:55]=1)([CH3:52])[CH3:51])([CH3:47])([CH3:46])[CH3:45].COC(=O)CC1C=CC=C(O)C=1.BrC(C)(C)C(OC(C)(C)C)=O>>[C:44]([O:48][C:49](=[O:64])[C:50]([O:53][C:54]1[CH:59]=[CH:58][CH:57]=[C:56]([CH2:60][C:61](=[O:62])[NH:10][C:9]2[C:4]([CH:1]3[CH2:2][CH2:3]3)=[N:5][C:6]([C:11]3[CH:16]=[CH:15][C:14]([C:17]([F:19])([F:20])[F:18])=[CH:13][CH:12]=3)=[N:7][CH:8]=2)[CH:55]=1)([CH3:52])[CH3:51])([CH3:46])([CH3:45])[CH3:47]

Participants

6

Reactant 5

HCID 39129Methyl 3-HydroxyphenylacetateHCID 90290tert-Butyl 2-bromo-2-methylpropionateHCID 187664143-(1-tert-Butoxycarbonyl-1-methylethoxy)phenylacetic AcidHCID 21935767HCID 21935767, compoundHCID 21935904HCID 21935904, compound

Product 1

HCID 69666999HCID 69666999, compound

Procedure

In analogy to the procedures described in example 26B] and 124C], 4-cyclopropyl-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-ylamine (prepared from 4-trifluoromethyl-2-(4-trifluoromethyl-phenyl)-pyrimidine-5-carboxylic acid, see example 133], in analogy to the procedures described in examples 125B] and 125C]) was reacted with 2-(3-carboxymethyl-phenoxy)-2-methyl-propionic acid tert-butyl ester (prepared from (3-hydroxy-phenyl)-acetic acid methyl ester and tert-butyl alpha-bromoisobutyrate, in analogy to the procedure described in example 52A], followed by saponification in analogy the procedure described in example 124A]) to give 2-(3-{[4-cyclopropyl-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-ylcarbamoyl]-methyl}-phenoxy)-2-methyl-propionic acid tert-butyl ester, which was subsequently cleaved with trifluoroacetic acid to yield the title compound as light yellow amorphous solid.

Sources & evidence

ORD record
ord-4eda39b34a3149bd8d93f340143fa7df
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

Loading…