Triethylamine → HCID 58514777, compound

HRID 449298Notes

Reaction equation

HRID 449298 reaction equation
CS(Cl)(=O)=O.[N:6]1[C:15]2[C:10](=[CH:11][C:12]([CH2:16][N:17]3[C:21]4=[N:22][C:23]([C:26]5[CH:27]=[N:28][N:29]([CH2:31][CH2:32]O)[CH:30]=5)=[CH:24][CH:25]=[C:20]4[N:19]=[N:18]3)=[CH:13][CH:14]=2)[CH:9]=[CH:8][CH:7]=1.C(N(CC)CC)C.[F-:41].[Cs+]>ClCCl.O.C(O)(C)(C)C>[F:41][CH2:32][CH2:31][N:29]1[CH:30]=[C:26]([C:23]2[N:22]=[C:21]3[N:17]([CH2:16][C:12]4[CH:11]=[C:10]5[C:15](=[CH:14][CH:13]=4)[N:6]=[CH:7][CH:8]=[CH:9]5)[N:18]=[N:19][C:20]3=[CH:25][CH:24]=2)[CH:27]=[N:28]1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 25953Cesium fluorideHCID 31297Methanesulfonyl chlorideHCID 53261809HCID 53261809, compound

Product 1

HCID 58514777HCID 58514777, compoundYield 10%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 6386tert-ButanolSolvent

Procedure

Methane sulphonyl chloride (0.069 g, 0.605 mmol) was added at 0° C. to a solution of example 146 (0.150 g, 0.403 mmol) and triethylamine (0.122 g, 1.21 mmol) in dichloromethane (3 ml) and warmed to RT. After 1 h, the mixture was diluted and washed with sodium bicarbonate solution, washed with brine, dried over sodium sulphate and concentrated. To the residue, cesium fluoride (0.270 g, 1.77 mmol) and tert-butanol (2 ml) were added and heated to 70° C. for 12 h. The reaction mixture was poured in water, extracted with ethyl acetate, washed with brine, dried over sodium sulphate and concentrated. The crude product was purified by column chromatography using dichloromethane: methanol to afford the title compound as an off-white solid (0.015 g, 10%). M.P.: 168-170° C. 1H-NMR (δ ppm, DMSO-d6, 400 MHz): 8.88 (dd, J=4.2, 1.7 Hz, 1H), 8.57 (s, 1H), 8.53 (d, J=8.7 Hz, 1H), 8.37 (d, J=7.4 Hz, 1H), 8.26 (s, 1H), 8.01 (d, J=8.1 Hz, 1H), 7.99 (s, 1H), 7.83 (m, 2H), 7.53 (dd, J=8.3, 4.2 Hz, 1H), 6.11 (s, 2H), 4.88 (dt, J=47.1, 4.5 Hz, 2H), 4.56 (dt, J=27.7, 4.8 Hz, 2H) MS (m/z):: 374.1 (M++1).

Workup

  1. additionthe mixture was diluted
  2. washwashed with sodium bicarbonate solution
  3. washwashed with brine
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated
  6. temperatureheated to 70° C. for 12 h
  7. extractionextracted with ethyl acetate
  8. washwashed with brine
  9. dry with materialdried over sodium sulphate
  10. concentrationconcentrated
  11. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-9ece2f47372c4a348bc5fcfa440d0cdc
Source dataset
uspto-grants-2013_07
Patent number
US08481739B2

Reaction notes

Loading…