Pyrrolidine → HCID 23728930, compound

HRID 1944699Notes

Reaction equation

HRID 1944699 reaction equation
[CH:1]1([N:4]2[CH2:9][CH2:8][N:7]([C:10]3[O:11][C:12]4[CH:18]=[CH:17][C:16]([C:19]([OH:21])=O)=[CH:15][C:13]=4[N:14]=3)[CH2:6][CH2:5]2)[CH2:3][CH2:2]1.[NH:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1.C(N(C(C)C)CC)(C)C.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>C1COCC1.O>[CH:1]1([N:4]2[CH2:9][CH2:8][N:7]([C:10]3[O:11][C:12]4[CH:18]=[CH:17][C:16]([C:19]([N:22]5[CH2:26][CH2:25][CH2:24][CH2:23]5)=[O:21])=[CH:15][C:13]=4[N:14]=3)[CH2:6][CH2:5]2)[CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 31268PyrrolidineHCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 59588788HCID 59588788, compound

Product 1

HCID 23728930HCID 23728930, compoundYield 35.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 2-(4-cyclopropylpiperazin-1-yl)benzooxazole-5-carboxylic acid (340 mg, 1.18 mmol), pyrrolidine (102 mg, 1.44 mmol) and diisopropylethylamine (372 mg, 2.88 mmol) in THF (5 mL) was added PyBop (1.25 g, 2.4 mmol) portionwise at 25° C. After stirring for 15 h, the mixture was diluted with water and extracted with ethyl acetate (3×10 mL). The combined organic extracts were washed with brine, dried (Na2SO4) and concentrated. The residue was purified by the preparative HPLC to give 141 mg (35%) of [2-(4-cyclopropylpiperazin-1-yl)benzooxazol-5-yl]pyrrolidin-1-ylmethanone as a trifluoroacetate salt.

Workup

  1. extractionextracted with ethyl acetate (3×10 mL)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customThe residue was purified by the preparative HPLC

Sources & evidence

ORD record
ord-261176168cb849f4a560f4f8bf14e8c9
Source dataset
uspto-grants-2013_03
Patent number
US08394842B2

Reaction notes

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