3-(Dimethylamino)pyrrolidine → HCID 11566630, compound

HRID 1268756Notes

Reaction equation

HRID 1268756 reaction equation
[CH3:1][N:2]([CH3:8])[CH:3]1[CH2:7][CH2:6][NH:5][CH2:4]1.Cl[C:10]1[CH:11]=[CH:12][N:13]2[C:18]([CH:19]=1)=[C:17]([CH2:20][CH3:21])[C:16]1[S:22][NH:23][C:24](=[O:25])[C:15]=1[C:14]2=[O:26]>CS(C)=O>[CH3:1][N:2]([CH3:8])[CH:3]1[CH2:7][CH2:6][N:5]([C:10]2[CH:11]=[CH:12][N:13]3[C:18]([CH:19]=2)=[C:17]([CH2:20][CH3:21])[C:16]2[S:22][NH:23][C:24](=[O:25])[C:15]=2[C:14]3=[O:26])[CH2:4]1

Participants

4

Reactant 2

HCID 27585193-(Dimethylamino)pyrrolidineHCID 11514675HCID 11514675, compound

Product 1

HCID 11566630HCID 11566630, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

(rac)-3-(Dimethylamino)pyrrolidine (30.0 μL, 0.239 mmol) is added to a yellow solution of 6 (11.4 mg, 0.041 mmol) in dimethyl sulfoxide (0.6 ml) at room temperature to give immediately an orange mixture. This mixture is irradiated in a microwave for 5 min. (120° C.; 300 W) to give an orange solution. The solution is evaporated under reduced pressure (˜1 mm Hg, 60° C.), and the remaining orange solid is washed with diethyl ether (3×15 mL) and water (3×15 mL). Subsequent drying in vacuo yields 7 as a yellow solid. Purity by HPLC: 97%; tR=10.86 min. mp 217–219° C. 1H NMR (DMSO-d6): δ1.11 (br t, J=6.5 Hz, 3H, CH2CH3), 1.85 (m, 1H, pyrrolidinyl H-4), 2.19 (m, 1H, pyrrolidinyl H-4′), 2.22 (s, 6H, N(CH3)2), 2.55 (br, 2H, CH2CH3), 2.84 (m, 1H, pyrrolidinyl H-3), 3.26 (m, 1H, pyrrolidinyl H-2), 3.44 (m, 1H, pyrrolidinyl H-5), 3.67 (m, 2H, overlapping pyrrolidinyl H-2′ and pyrrolidinyl H-5′), 6.14 (br, 1H, pyridone H-8), 6.84 (br d, J=8.0 Hz, 1H, pyridone H-6), 8.86 (d, J=8.0 Hz, 1H, pyridone H-5). 13C{1H} NMR (DMSO-d6): δ12.1 (CH2CH3), 21.8 (CH2CH3), 29.1 (pyrrolidinyl C-4), 43.8 (N(CH3)2), 46.9 (pyrrolidinyl C-5), 51.8 (pyrrolidinyl C-2), 64.6 (pyrrolidinyl C-3), 92.5 (C-8, CH), 95.7 (C-3a), 99.9 (C-9), 105.9 (C-6, CH), 129.3 (C-5, CH), 141.8 (C-8a), 148.3 (C-7, C—N), 153.3 (C-4, NC(O)), 154.9 (C-9a, C—S), 167.9 (C-3, CONS). LCMS m/z calcd for C18H22N4O2S 358 ([M+]); found 359 ([M+H]+). HRMS m/z calcd for C18H22N4NaO2S 381.1361 ([M+Na]+); found 381.1366. Anal. Calcd. for C18H22N4O2S.H2O: C, 57.43; H, 6.43; N, 14.88. Found: C, 57.29; H, 6.08; N, 14.87.

Workup

  1. customto give immediately an orange mixture
  2. customThis mixture is irradiated in a microwave for 5 min. (120° C.; 300 W)
  3. customto give an orange solution
  4. customThe solution is evaporated under reduced pressure (˜1 mm Hg, 60° C.)
  5. washthe remaining orange solid is washed with diethyl ether (3×15 mL) and water (3×15 mL)
  6. customSubsequent drying in vacuo

Sources & evidence

ORD record
ord-3670401260c042799553e65f29bf1658
Source dataset
uspto-grants-2007_04
Patent number
US07199128B2

Reaction notes

Loading…