2-Aminothiazole → HCID 21094184, compound

HRID 1350306Notes

Reaction equation

[C:1]([CH:4]([C:12]1[CH:21]=[CH:20][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][CH:13]=1)[CH2:5][CH:6]1[CH2:11][CH2:10][O:9][CH2:8][CH2:7]1)([OH:3])=O.[S:22]1[CH:26]=[CH:25][N:24]=[C:23]1[NH2:27]>>[O:9]1[CH2:10][CH2:11][CH:6]([CH2:5][CH:4]([C:12]2[CH:21]=[CH:20][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][CH:13]=2)[C:1](=[O:3])[NH:27][C:23]2[S:22][CH:26]=[CH:25][N:24]=2)[CH2:7][CH2:8]1

Participants

Reactant 2

HCID 21552-Aminothiazole

HCID 21094182HCID 21094182, compound

Product 1

HCID 21094184HCID 21094184, compound

Procedure

Methyl 4-tert-butoxycarbonylmethylbenzoate (1.71 g, 6.84 mmol) was alkylated with 4-iodomethyltetrahydropyran (1.86 g, 8.21 mmol), employing the method described in Preparation 41, to afford methyl 4-[1-tert-butoxycarbonyl-2-(tetrahydropyran-4-yl)ethyl]benzoate: RTA=3.86 min. A solution of this compound (1.37 g, 3.94 mmol) in CH2Cl2 (5 mL) was treated with TFA-CH2Cl2 (2:1, 15 mL) at 0° C. over 10 min. The mixture was stirred at 20° C. for 3 h, before being concentrated in vacuo. The residue was treated with PhMe and the solvents were evaporated off under reduced pressure. This process was repeated twice to provide crude methyl 4-[1-carboxy-2-(tetrahydropyran-4-yl)ethyl]benzoate. This carboxylic acid was condensed with thiazol-2-ylamine, utilizing the protocol outlined in EXAMPLE 65, to furnish methyl 4-[2-(tetrahydropyran-4-yl)-1-(thiazol-2-ylcarbamoyl)ethyl]benzoate: m/z (ES+)=375.2 [M+H]+. This ester (1.20 g, 3.21 mmol) was saponified with LiOH.H2O, using the procedure described in Preparation 22, to furnish the title compound: m/z (ES−)=359.2 [M−H]−.

Sources & evidence

ORD record: ord-f1347bb5aa624e1eabc03b07cb256d32
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07214681B2

Reaction notes

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