Water → N-tert-butyl-2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine hydrochloride

HRID 29114Notes

Reaction equation

HRID 29114 reaction equation
[C:1]([NH:5][C:6]1[N:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]2=[N:8][C:7]=1[C:15]1[S:16][C:17]([C:20]#[C:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=2)=[CH:18][CH:19]=1)([CH3:4])([CH3:3])[CH3:2].O.[Cl:29][Si](C)(C)C>C(Cl)Cl>[ClH:29].[C:1]([NH:5][C:6]1[N:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]2=[N:8][C:7]=1[C:15]1[S:16][C:17]([C:20]#[C:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=2)=[CH:18][CH:19]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 962WaterHCID 6397ChlorotrimethylsilaneHCID 11603179N-tert-butyl-2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine

Product 1

HCID 11603916N-tert-butyl-2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine hydrochlorideYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 6.93 g (18.6 mmol) of N-tert-butyl-2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine (Example 94) in DCM (180 ml) was combined with 335 μl (18.6 mmol) of water and 2.35 ml (18.6 mmol) of chlorotrimethylsilane and stirred at RT for 16 h. The resultant precipitate was filtered out and dried under a vacuum at 40° C., 6.09 g (14.8 mmol, 80%) of N-tert-butyl-2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine hydrochloride being obtained.

Workup

  1. filtrationThe resultant precipitate was filtered out
  2. customdried under a vacuum at 40° C.

Sources & evidence

ORD record
ord-61ab15063f574b73b2621fd6ccd62d16
Source dataset
uspto-grants-2008_09
Patent number
US07420056B2

Reaction notes

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