1-Iodopropane → HCID 66630224, compound

HRID 426377Notes

Reaction equation

HRID 426377 reaction equation
[CH2:1]([C:4]([C:11]1[CH:16]=[CH:15][C:14]([C:17]2[NH:18][C:19]3[CH:25]=[C:24]([C:26]#[N:27])[C:23]([C:28]#[N:29])=[CH:22][C:20]=3[N:21]=2)=[CH:13][CH:12]=1)([CH2:8][CH:9]=[CH2:10])[CH2:5][CH:6]=[CH2:7])[CH:2]=[CH2:3].[CH2:30]1[CH2:40]CN2C(=NCCC2)C[CH2:31]1.ICCC>CN1C(=O)CCC1.C(OCC)(=O)C>[CH2:1]([C:4]([C:11]1[CH:16]=[CH:15][C:14]([C:17]2[N:21]([CH2:31][CH2:30][CH3:40])[C:20]3[CH:22]=[C:23]([C:28]#[N:29])[C:24]([C:26]#[N:27])=[CH:25][C:19]=3[N:18]=2)=[CH:13][CH:12]=1)([CH2:8][CH:9]=[CH2:10])[CH2:5][CH:6]=[CH2:7])[CH:2]=[CH2:3]

Participants

6

Reactant 3

HCID 336431-Iodopropane3×HCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene3×HCID 66629483HCID 66629483, compound

Product 1

HCID 66630224HCID 66630224, compoundYield 62.2%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Following a reported procedure, a sample of 3 (265 mg, 0.70 mmol) in NMP (2.5 mL) was heated to 120° C. and treated with DBU (105 μL, 0.70 mmol). After stirring for 2 min, iodopropane (105 μL, 0.70 mmol) was added and the mixture was stirred for 15 min. A second dose of DBU (68 μL, 0.70 mmol), followed by iodopropane (68 μL, 0.70 mmol), was added, and 15 min later, a third identical round of DBU and iodopropane was again added. After the mixture was stirred for 15 min, the reaction mixture was allowed to cool and was diluted with ethyl acetate. The organic solution was washed with water and brine. The organic layer was dried (Na2SO4), filtered, concentrated, and chromatographed (silica, CH2Cl2 w/ethyl acetate gradient of 0-5%). Some starting material was recovered (83 mg, 31%), and fractions containing the product were concentrated to give a colorless solid (183 mg, 62%): mp 132-134° C.; 1H NMR δ 0.92 (t, J=8.0 Hz, 3H), 1.82-1.93 (m, 2H), 2.52 (d, J=8.8 Hz, 6H), 4.31 (t, J=7.6 Hz, 2H), 4.98-5.09 (m, 6H), 5.50-5.63 (3H), 7.53 (d, J=8.4 Hz, 2H), 7.70 (d, J=8.4 Hz, 2H), 7.88 (s, 1H), 8.19 (s, 1H); 13C NMR δ 11.4, 23.5, 41.9, 44.1, 47.3, 108.5, 109.0, 116.7, 116.8, 118.5, 126.1, 126.4, 127.9, 129.2, 134.0, 137.9, 145.4, 149.9, 159.4; Anal. Calcd for C28H28N4: C, 79.97; H, 6.71; N, 13.32. Found: C, 79.93; H, 6.73; N, 13.35.

Workup

  1. stirringthe mixture was stirred for 15 min
  2. additionwas added
  3. stirringAfter the mixture was stirred for 15 min
  4. temperatureto cool
  5. washThe organic solution was washed with water and brine
  6. dry with materialThe organic layer was dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customchromatographed (silica, CH2Cl2 w/ethyl acetate gradient of 0-5%)
  10. customSome starting material was recovered (83 mg, 31%), and fractions
  11. additioncontaining the product
  12. concentrationwere concentrated

Sources & evidence

ORD record
ord-b4450d49e4024035ad17421d4ee1030c
Source dataset
uspto-grants-2012_01
Patent number
US08106393B2

Reaction notes

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