Diisopropylethylamine → HCID 87464014, compound

HRID 1260361Notes

Reaction equation

HRID 1260361 reaction equation
[I-].C[N+]1C=CN([C:8](=[O:30])/[N:9]=[C:10]2\[S:11][C:12]([CH3:29])=[CH:13][N:14]\2[C:15]2[CH:28]=[CH:27][C:18]3[O:19][C:20]([F:26])([F:25])[C:21]([F:24])([F:23])[O:22][C:17]=3[CH:16]=2)C=1.[NH:31]1[CH2:35][CH2:34][C@H:33]([OH:36])[CH2:32]1.CCN(C(C)C)C(C)C>C(#N)C.C(Cl)Cl>[OH:36][C@H:33]1[CH2:34][CH2:35][N:31]([C:8](/[N:9]=[C:10]2\[S:11][C:12]([CH3:29])=[CH:13][N:14]\2[C:15]2[CH:28]=[CH:27][C:18]3[O:19][C:20]([F:26])([F:25])[C:21]([F:23])([F:24])[O:22][C:17]=3[CH:16]=2)=[O:30])[CH2:32]1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 2733874(3S)-pyrrolidin-3-olHCID 87462668HCID 87462668, compound

Product 1

HCID 87464014HCID 87464014, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of (Z)-3-methyl-1-(5-methyl-3-(2,2,3,3-tetrafluoro-2,3-dihydrobenzo[b][1,4]dioxin-6-yl)thiazol-2(3H)-ylidenecarbamoyl)-1H-imidazol-3-ium iodide (Example 81A, 0.1 g, 0.18 mmol), (S)-pyrrolidin-3-ol (0.016 g, 0.18 mmol) and Hunig's base (0.023 g, 018 mmol) in dry acetonitrile (5 mL) was heated to 60° C. for three hours. After cooling, the mixture was diluted with CH2Cl2 (50 mL) and washed with water and brine. The organic phase was dried over sodium sulfate, filtered and dried. After evaporation under reduced pressure, the residue was chromatographed over silica using CH2Cl2 and then 2% MeOH/CH2Cl2 to give the titled compound. 1H NMR (CDCl3) δ ppm 1.99 (2 H), 2.20 (3 H), 3.40-3.70 (4 H), 4.42 (1 H), 6.60 (1 H), 7.20-7.50 (3 H); MS (ESI) m/z 434(M+H)+.

Workup

  1. temperatureAfter cooling
  2. washwashed with water and brine
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. filtrationfiltered
  5. customdried
  6. customAfter evaporation under reduced pressure
  7. customthe residue was chromatographed over silica

Sources & evidence

ORD record
ord-2930cde6d2014f978e1113822717eee5
Source dataset
uspto-grants-2013_06
Patent number
US08470813B2

Reaction notes

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