Pyrrolidine → HCID 9945660, compound

HRID 1268675Notes

Reaction equation

HRID 1268675 reaction equation
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:13]=[C:14]3[CH:19]=[C:18]([CH3:20])[CH:17]=[CH:16][N:15]3[CH:21]=2)=[CH:8][CH:7]=1.[NH:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1>>[N:22]1([CH2:2][CH2:3][CH2:4][O:5][C:6]2[CH:11]=[CH:10][C:9]([C:12]3[N:13]=[C:14]4[CH:19]=[C:18]([CH3:20])[CH:17]=[CH:16][N:15]4[CH:21]=3)=[CH:8][CH:7]=2)[CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

3

Reactant 2

HCID 31268PyrrolidineHCID 142014602-(4-Chloropropoxyphenyl)-7-methylimidazo[1,2-a]pyridine

Product 1

HCID 9945660HCID 9945660, compound

Procedure

The product of Step C, Example 8 (126 mg) and pyrrolidine (1.5 mL) were heated at 85° C. for 4 hours. The reaction was cooled to ambient temperature and partitioned between ethyl acetate (6 mL) and half-saturated sodium bicarbonate solution (6 mL). The aqueous portion was extracted with additional ethyl acetate (6 mL) and the organic portions combined and evaporated. The residue was purified via silica gel chromatography (dichloromethane/methanol) to give the title compound (50.3 mg). 1H-NMR (CD3OD) δ 8.18 (d, 7.0 Hz, 1H), 7.91 (s, 1H), 7.77 (m, 2H), 7.25 (s, 1H), 6.94 (m, 2H), 6.68 (m, 1H), 4.01 (t, J=6.0 Hz, 2H), 2.71 (m, 2H), 2.64 (m, 4H), 2.37 (s, 3H), 2.01 (m, 2H), 1.83 (m, 4H)

Workup

  1. custompartitioned between ethyl acetate (6 mL) and half-saturated sodium bicarbonate solution (6 mL)
  2. extractionThe aqueous portion was extracted with additional ethyl acetate (6 mL)
  3. customevaporated
  4. customThe residue was purified via silica gel chromatography (dichloromethane/methanol)

Sources & evidence

ORD record
ord-7f61bf25a7f74437ab05a020bacee63c
Source dataset
uspto-grants-2007_04
Patent number
US07199117B2

Reaction notes

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