Pyrrolidine → HCID 178474509, compound

HRID 1260347Notes

Reaction equation

HRID 1260347 reaction equation
Cl[CH2:2][C:3]1[S:7]/[C:6](=[N:8]\[C:9](=[O:11])[CH3:10])/[N:5]([C:12]2[CH:22]=[CH:21][C:15]3[O:16][C:17]([F:20])([F:19])[O:18][C:14]=3[CH:13]=2)[CH:4]=1.[NH:23]1[CH2:27][CH2:26][CH2:25][CH2:24]1>>[F:19][C:17]1([F:20])[O:16][C:15]2[CH:21]=[CH:22][C:12]([N:5]3[CH:4]=[C:3]([CH2:2][N:23]4[CH2:27][CH2:26][CH2:25][CH2:24]4)[S:7]/[C:6]/3=[N:8]\[C:9](=[O:11])[CH3:10])=[CH:13][C:14]=2[O:18]1

Participants

3

Reactant 2

HCID 31268PyrrolidineHCID 178474507HCID 178474507, compound

Product 1

HCID 178474509HCID 178474509, compound

Procedure

The allyl chloride (Example 24A, 16 mg, 46 μmol) was dissolved into pyrrolidine (200 μL) and stirred 10 minutes. Then the mixture was twice diluted with and concentrated from EtOAc, and partitioned between 2:1 EtOAc/hexanes (1.5 mL) and water (1 mL). The organic phase was separated and washed with water, dried (Na2SO4), and chromatographed on silica (2 to 5% MeOH/CH2Cl2) to give the titled compound. 1H NMR (300 MHz, CDCl3) δ ppm 1.81 (4 H), 2.22 (3 H), 2.60 (4 H), 3.66 (2 H), 6.91 (1 H), 7.17 (2 H), 7.36 (1 H); MS (ESI) 382 (M+H)+.

Workup

  1. additionThen the mixture was twice diluted with and
  2. concentrationconcentrated from EtOAc
  3. custompartitioned between 2:1 EtOAc/hexanes (1.5 mL) and water (1 mL)
  4. customThe organic phase was separated
  5. washwashed with water
  6. dry with materialdried (Na2SO4)
  7. customchromatographed on silica (2 to 5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-490adf19b5b34d4481f78849f7de7b50
Source dataset
uspto-grants-2013_06
Patent number
US08470813B2

Reaction notes

Loading…