Pyrrolidine → HCID 58332219, compound

HRID 1891407Notes

Reaction equation

HRID 1891407 reaction equation
Br[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:10]=[C:9]([C:11]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([F:20])=[C:16]([Cl:21])[CH:15]=2)=[O:12])[O:8][N:7]=1.[NH:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1>O1CCCC1.CO>[Cl:21][C:16]1[CH:15]=[C:14]([NH:13][C:11]([C:9]2[O:8][N:7]=[C:6]([O:5][CH2:4][CH2:3][CH2:2][N:22]3[CH2:26][CH2:25][CH2:24][CH2:23]3)[CH:10]=2)=[O:12])[CH:19]=[CH:18][C:17]=1[F:20]

Participants

5

Reactant 2

HCID 31268PyrrolidineHCID 59799399HCID 59799399, compound

Product 1

HCID 58332219HCID 58332219, compoundYield 92.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-(3-bromopropoxy)-N-(3-chloro-4-fluorophenyl)isoxazole-5-carboxamide (38 mg, 0.10 mmol), and pyrrolidine (100 μL, 1.20 mmol) in tetrahydrofuran (1.5 mL) was stirred at room temperature for 4 h. The reaction was diluted with methanol and purified by preparative LCMS to give the desired product (34 mg, 92%). MF=C17H20ClFN3O3; LCMS calculated for C17H20ClFN3O3 (M+H)+: m/z=368.

Workup

  1. custompurified by preparative LCMS

Sources & evidence

ORD record
ord-95a3a07108f641c6812d40ecbe3569d7
Source dataset
uspto-grants-2013_08
Patent number
US08507541B2

Reaction notes

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