Triethylamine → HCID 10309371, compound

HRID 1060695Notes

Reaction equation

HRID 1060695 reaction equation
Cl[CH2:2][CH2:3][CH2:4][S:5](Cl)(=[O:7])=[O:6].[NH2:9][CH2:10][CH2:11][CH2:12][CH2:13][N:14]1[C:22]2[C:21]([CH3:23])=[C:20]([CH3:24])[N:19]=[C:18]([NH2:25])[C:17]=2[N:16]=[C:15]1[CH2:26][CH2:27][CH3:28].C(N(CC)CC)C.N12CCCN=C1CCCCC2>ClCCl.C(#N)C.O>[O:6]=[S:5]1(=[O:7])[CH2:4][CH2:3][CH2:2][N:9]1[CH2:10][CH2:11][CH2:12][CH2:13][N:14]1[C:22]2[C:21]([CH3:23])=[C:20]([CH3:24])[N:19]=[C:18]([NH2:25])[C:17]=2[N:16]=[C:15]1[CH2:26][CH2:27][CH3:28]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 154103-Chloropropanesulphonyl chlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 22499148HCID 22499148, compound

Product 1

HCID 10309371HCID 10309371, compoundYield 76.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

Chloropropanesulfonyl chloride (0.221 mL, 1.82 mmol) was added drop wise to a chilled (0° C.) solution of 1-(4-aminobutyl)-6,7-dimethyl-2-propyl-1H-imidazo[4,5-c]pyridin-4-amine (0.500 g, 1.82 mmol) in dichloromethane (10 mL). The reaction mixture was allowed to stir for 20 minutes after the addition was completed then triethylamine (0.245 mL, 2.51 mmol) was added drop wise. The reaction mixture was allowed to stir for 20 minutes after the addition was completed then it was poured into water. The layers were separated. The organic layer was washed with brine, dried over magnesium sulfate and then concentrated under reduced pressure. The residue was dissolved in N,N-dimethylformamide (10 mL). 1,8-Diazabicyclo[5.4.0]undec-7-ene (0.272 mL, 1.82 mmol) was added and the reaction mixture was allowed to stir overnight. The reaction mixture was poured into water and then extracted with chloroform (×3). The combined extracts were washed with water then with brine, dried over magnesium sulfate and then concentrated under reduced pressure to provide a yellowish oil. The oil was dissolved in acetonitrile and then concentrated under reduced pressure to provide a yellowish white solid. This material was recrystallized from isopropanol to provide 0.53 g of 1-[4-(1,1-dioxidoisothiazolidin-2-yl)butyl]-6,7-dimethyl-2-propyl-1H-imidazo[4,5-c]pyridin-4-amine as a yellow orange solid, m.p. 155.1-161.2° C. Analysis: Calculated for C18H29N5O2S: % C, 56.97; % H, 7.70; % N, 18.45; Found: % C, 56.61; % H, 7.77; % N, 18.14. 1H NMR (300 MHz, DMSO-d6) δ 5.67 (s, 2H), 4.21 (apparent t, J=7.5 Hz, 2H), 3.2-3.08 (m, 4H), 2.92 (t, J=6.5 Hz, 2H), 2.77 (t, J=7.5 Hz, 2H), 2.37 (s, 3H), 2.30 (s, 3H), 2.19 (quintet, J=6.7 Hz, 2H), 1.78 (sextet, J=7.4 Hz, 2H), 1.73-1.55 (m, 4H), 1.00 (t, J=7.4 Hz, 3H); MS(CI) m/e 380.2117 (380.2120 calcd for C18H29N5O2S, M+H).

Workup

  1. additionafter the addition
  2. stirringto stir for 20 minutes
  3. additionafter the addition
  4. customThe layers were separated
  5. washThe organic layer was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. dissolutionThe residue was dissolved in N,N-dimethylformamide (10 mL)
  9. stirringto stir overnight
  10. extractionextracted with chloroform (×3)
  11. washThe combined extracts were washed with water
  12. dry with materialwith brine, dried over magnesium sulfate
  13. concentrationconcentrated under reduced pressure
  14. customto provide a yellowish oil
  15. concentrationconcentrated under reduced pressure
  16. customto provide a yellowish white solid
  17. customThis material was recrystallized from isopropanol

Sources & evidence

ORD record
ord-92e17d951bc5402889d9a5fd1d43468d
Source dataset
uspto-grants-2003_02
Patent number
US06525064B1

Reaction notes

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