4-Fluorobenzamide → HCID 66762338, compound

HRID 2249593Notes

Reaction equation

HRID 2249593 reaction equation
[CH3:1][C:2]1[S:6][C:5]([C:7]2[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][N:8]=2)=[N:4][C:3]=1[CH2:17][CH2:18]O.FC(F)(F)[C:22]1[CH:23]=[CH:24][C:25]([C:28](=S)[NH2:29])=[N:26][CH:27]=1.C[O:34]C(=O)CC(=O)C(Br)C.FC1C=CC([C:48]([NH2:50])=O)=CC=1>>[CH3:1][C:2]1[S:6][C:5]([C:7]2[CH:12]=[CH:11][C:10]([C:13]([F:14])([F:15])[F:16])=[CH:9][N:8]=2)=[N:4][C:3]=1[CH2:17][CH2:18][NH:50][CH2:48][C:27]([N:26]1[CH2:22][CH2:23][CH2:24][C@H:25]1[C:28]#[N:29])=[O:34]

Participants

5

Reactant 4

HCID 715724-FluorobenzamideHCID 27777735-(trifluoromethyl)pyridine-2-carbothioamideHCID 9815681Methyl 4-bromo-3-oxopentanoateHCID 22563305HCID 22563305, compound

Product 1

HCID 66762338HCID 66762338, compound

Procedure

The title compound was prepared in analogy to example 31 (steps A] and C] as outlined for example 31 and step B] according to example 33) starting from 2-[5-methyl-2-(5-trifluoromethyl-pyridin-2-yl)-thiazol-4-yl]-ethanol. This starting material could be prepared from 5-trifluoromethyl-2-pyridinecarbothioamide [CAS 175277-51-7, commercially available] and methyl-4-bromo-3-oxopentanoate with 4-fluoro-benzamide as described in Collins, J. L. et al. J. Med. Chem. 1998, 41, 5037-5054. The compound was obtained as a yellow gum.

Workup

  1. customThe compound was obtained as a yellow gum

Sources & evidence

ORD record
ord-23eb5a64c3d84fe7b3b45c74e474bfe6
Source dataset
uspto-grants-2008_01
Patent number
US07314884B2

Reaction notes

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