2-Bromo-4-(trifluoromethyl)-1,3-thiazole → Tert-butyl[tert-butoxycarbonyl(6-{(pyridin-2-ylsulfonyl)[4-(4-trifluoromethylthiazol-2-yl)benzyl]aminomethyl}pyridin-2-yl)amino]acetate

HRID 241266Notes

Reaction equation

HRID 241266 reaction equation
[C:1]([O:5][C:6](=[O:49])[CH2:7][N:8]([C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH:15]([S:33]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=2)(=[O:35])=[O:34])[NH:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21](B3OC(C)(C)C(C)(C)O3)=[CH:20][CH:19]=2)[N:10]=1)([CH3:4])([CH3:3])[CH3:2].Br[C:51]1[S:52][CH:53]=[C:54]([C:56]([F:59])([F:58])[F:57])[N:55]=1>>[C:1]([O:5][C:6](=[O:49])[CH2:7][N:8]([C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH:15]([S:33]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=2)(=[O:35])=[O:34])[NH:16][CH2:17][C:18]2[CH:19]=[CH:20][C:21]([C:51]3[S:52][CH:53]=[C:54]([C:56]([F:59])([F:58])[F:57])[N:55]=3)=[CH:22][CH:23]=2)[N:10]=1)([CH3:3])([CH3:4])[CH3:2]

Participants

3

Reactant 2

HCID 231498872-Bromo-4-(trifluoromethyl)-1,3-thiazoleHCID 86651786Tert-butyl [tert-butoxycarbonyl(6-{(pyridin-2-ylsulfonyl)[4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)benzyl]aminomethyl}pyridin-2-yl)amino]acetate

Product 1

HCID 86651785Tert-butyl[tert-butoxycarbonyl(6-{(pyridin-2-ylsulfonyl)[4-(4-trifluoromethylthiazol-2-yl)benzyl]aminomethyl}pyridin-2-yl)amino]acetateYield 90%

Procedure

Reaction and post-treatment were carried out in the same manner as in Example 22-(c) except for using tert-butyl[tert-butoxycarbonyl(6-{(pyridin-2-ylsulfonyl)[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)benzyl]aminomethyl}pyridin-2-yl)amino]acetate (490 mg, containing 0.700 mmol of a pure content) obtained in Example 22-(b), and using 2-bromo-4-trifluoromethylthiazole (see WO 2005/077912A) (341 mg, 1.47 mmol) in place of 2-bromo-5-methylthiazole to afford the title compound (454 mg) as a white foam. (Yield: 90%)

Workup

  1. customReaction
  2. additioncontaining 0.700 mmol of a pure content)
  3. customobtained in Example 22-(b)

Sources & evidence

ORD record
ord-91f923122d1d46a9b5796fc9b3f3a744
Source dataset
uspto-grants-2014_02
Patent number
US08648097B2

Reaction notes

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