Hydrogen chloride-ethyl acetate → 1'-(2-aminoacetyl)-5-bromo-N-(5-chlorothiazol-2-yl)spiro[indoline-3,3'-pyrrolidine]-1-carboxamide
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:10]3([CH2:14][CH2:13][N:12]([C:15](=[O:25])[CH2:16][NH:17]C(=O)OC(C)(C)C)[CH2:11]3)[CH2:9][N:8]([C:26](=[O:34])[NH:27][C:28]3[S:29][C:30]([Cl:33])=[CH:31][N:32]=3)[C:5]2=[CH:6][CH:7]=1.Cl.C(OCC)(=O)C>C(OCC)(=O)C>[NH2:17][CH2:16][C:15]([N:12]1[CH2:13][CH2:14][C:10]2([C:4]3[C:5](=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=3)[N:8]([C:26]([NH:27][C:28]3[S:29][C:30]([Cl:33])=[CH:31][N:32]=3)=[O:34])[CH2:9]2)[CH2:11]1)=[O:25]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
The t-butyl (2-(5-bromo-1-((5-chlorothiazol-2-yl)carbamoyl)spiro[indoline-3,3′-pyrrolidin]-1′-yl)-2-oxoethyl)carbamate (18 mg, 0.032 mmol) obtained in Example 19 was dissolved in ethyl acetate (0.5 mL). Thereafter, a 4 N solution of HCl/ethyl acetate (200 μL, 0.800 mmol) was added to the above obtained solution at room temperature, and the obtained mixture was then stirred for 7 hours. Thereafter, the reaction solution was neutralized, was then filtered, and was then concentrated in vacuo. The obtained residue was purified by silica gel column chromatography (chloroform:ammonia-methanol=10:1) to obtain the captioned compound in the form of a light yellow solid.
Workup
- filtrationwas then filtered
- concentrationwas then concentrated in vacuo
- customThe obtained residue was purified by silica gel column chromatography (chloroform:ammonia-methanol=10:1)
- customto obtain the captioned compound in the form of a light yellow solid
Sources & evidence
- ORD record
- ord-dd284ec5fc174aeebb2d3abd258eb435
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08921576B2
Reaction notes
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