Reaction equation
C[O:2][C:3]([C:5]1[C:6]2[N:7]([C:11]([NH:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[C:12]([C:14]3[S:15][C:16]([C:19]#[C:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[CH:17][CH:18]=3)[N:13]=2)[CH:8]=[CH:9][N:10]=1)=[O:4].[OH-].[Na+].C(O)(=O)C.C(Cl)Cl.CCCCCC>CO.CC#N>[C:28]([NH:27][C:11]1[N:7]2[CH:8]=[CH:9][N:10]=[C:5]([C:3]([OH:4])=[O:2])[C:6]2=[N:13][C:12]=1[C:14]1[S:15][C:16]([C:19]#[C:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[CH:17][CH:18]=1)([CH3:31])([CH3:29])[CH3:30]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of 200 mg (0.47 mmol) of 3-(tert-butylamino)-2-(5-(phenylethynyl)-thiophen-2-yl)imidazo[1,2-a]pyrazine-8-carboxylic acid methyl ester (Example 106) in a mixture of MeOH (5 ml) and MeCN (5.5 ml) was combined with 5 ml (0.51 mmol) of a 0.1M aq. NaOH solution and stirred at RT for 1 h. The reaction mixture was then combined with 26 μl of a 5 N aq. acetic acid solution. The solvents were then largely removed by distillation under a vacuum. The residual aq. phase was repeatedly extracted with EA. The combined organic phases were dried over MgSO4, filtered and evaporated under a vacuum. 87 mg (0.21 mmol, 44%) of 3-(tert-butylamino)-2-(5-(phenylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazine-8-carboxylic acid were obtained by crystallisation of the group from DCM/hexane (1:2).
Workup
- customThe solvents were then largely removed by distillation under a vacuum
- extractionThe residual aq. phase was repeatedly extracted with EA
- dry with materialThe combined organic phases were dried over MgSO4
- filtrationfiltered
- customevaporated under a vacuum
Sources & evidence
- ORD record
- ord-affc0f0e005b44849087fa00051a3ccd
- Source dataset
- uspto-grants-2008_09
- Patent number
- US07420056B2
Linked notes
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