Pyrrolidine → (2-Chloro-5-phenyl-thiophen-3-yl)-(pyrrolidin-1-yl)-methanone

HRID 1914538Notes

Reaction equation

HRID 1914538 reaction equation
[Cl:1][C:2]1[S:3][C:4]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:5][C:6]=1[C:7]([OH:9])=O.CC[N:18]([CH:22]([CH3:24])C)[CH:19]([CH3:21])C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.N1CCCC1>CN(C=O)C>[Cl:1][C:2]1[S:3][C:4]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:5][C:6]=1[C:7]([N:18]1[CH2:19][CH2:21][CH2:24][CH2:22]1)=[O:9]

Participants

6

Reactant 4

HCID 31268PyrrolidineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 581102042-Chloro-5-phenylthiophene-3-carboxylic acid

Product 1

HCID 44226477(2-Chloro-5-phenyl-thiophen-3-yl)-(pyrrolidin-1-yl)-methanoneYield 252.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Chloro-5-phenyl-thiophene-3-carboxylic acid (28 mg, 0.11 mmol) was dissolved in DMF (1 mL). DIPEA (0.22 mmol), HATU (0.11 mmol) and pyrrolidine (0.11 mmol) were added and the reaction mixture stirred at room temperature. The reaction mixture was partitioned between ethyl acetate and 1 N hydrochloric acid. The organic solution was separated and dried over magnesium sulfate, filtered and the solvent evaporated. The residue was purified by preparative HPLC, eluting with 50%-90% acetonitrile in water (0.1% formic acid) over 30 minutes. The fractions containing the desired product were concentrated under vacuum to give the title compound (81 mg). LCMS m/z 292.10 [M+H]+ R.T.=11.27 mins (Analytical Method 1)

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and 1 N hydrochloric acid
  2. customThe organic solution was separated
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customthe solvent evaporated
  6. customThe residue was purified by preparative HPLC
  7. washeluting with 50%-90% acetonitrile in water (0.1% formic acid) over 30 minutes
  8. additionThe fractions containing the desired product
  9. concentrationwere concentrated under vacuum

Sources & evidence

ORD record
ord-72897775bc0a4a9aae099f59bc279c21
Source dataset
uspto-grants-2013_12
Patent number
US08614209B2

Reaction notes

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