Ammonia → Benzo[b]thiophene-2,7-dicarboxamide, 3-amino-4-(cyclobutyloxy)-
Reaction equation
[C:1]([C:3]1[C:4](F)=[C:5]([CH:9]=[CH:10][C:11]=1[O:12][CH:13]1[CH2:16][CH2:15][CH2:14]1)[C:6]([OH:8])=O)#[N:2].N.C([N:22](C(C)C)CC)(C)C.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.[SH:61][CH2:62][C:63]([NH2:65])=[O:64].[O-]CC.[Na+]>C1COCC1.[OH-].[Na+]>[NH2:2][C:1]1[C:3]2[C:11]([O:12][CH:13]3[CH2:16][CH2:15][CH2:14]3)=[CH:10][CH:9]=[C:5]([C:6]([NH2:22])=[O:8])[C:4]=2[S:61][C:62]=1[C:63]([NH2:65])=[O:64]Participants
Reactant 6
Product 1
Reagents, catalysts & solvents 2
Procedure
To a stirred solution of the above benzoic acid intermediate (2.00 g, 8.50 mmol) in THF (20 mL) was added an ammonia solution (0.5M in 1,4-dioxane, 17.0 mL, 8.50 mmol), diisopropylethylamine (3.36 g, 26.0 mmol) and PyBOP (4.43 g, 8.50 mmol). The solution was stirred at room temperature overnight then 2-mercaptoacetamide (1.1 M in MeOH, 11.6 mL, 12.76 mmol) was added and the reaction was heated at 80° C. for 3 h. Sodium ethoxide (2.68 M in EtOH, 4.80 mL, 12.86 mmol) was added and the reaction continued for 4 h. After cooling to room temperature, the reaction was diluted with 2 N sodium hydroxide solution (100 mL). The precipitate formed was collected by filtration, washed with MeOH and dried in vacuo to give 3-amino-4-cyclobutoxy-benzo[b]thiophene-2,7-dicarboxylic acid diamide (0.850 g, 2.784 mmol, 32.7%).
Workup
- temperaturethe reaction was heated at 80° C. for 3 h
- waitthe reaction continued for 4 h
- temperatureAfter cooling to room temperature
- customThe precipitate formed
- filtrationwas collected by filtration
- washwashed with MeOH
- customdried in vacuo
Sources & evidence
- ORD record
- ord-4e71a625831843d78858689125fdc29c
- Source dataset
- uspto-grants-2008_02
- Patent number
- US07329764B2
Reaction notes
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