(Diethylamino)sulfur trifluoride → HCID 11478611, compound

HRID 749417Notes

Reaction equation

HRID 749417 reaction equation
C(N(S(F)(F)[F:7])CC)C.[C:10]([C:12]1[CH:13]=[C:14]([C:22]([N:24]([CH2:26][C@H:27]([C:41]2[CH:46]=[CH:45][C:44]([Cl:47])=[C:43]([Cl:48])[CH:42]=2)[CH2:28][CH2:29][N:30]2[CH2:33][CH:32]([N:34]3[CH2:39][CH2:38][C:37](=O)[CH2:36][CH2:35]3)[CH2:31]2)[CH3:25])=[O:23])[C:15]2[C:20]([CH:21]=1)=[CH:19][CH:18]=[CH:17][CH:16]=2)#[N:11]>C(Cl)Cl>[C:10]([C:12]1[CH:13]=[C:14]([C:22]([N:24]([CH2:26][C@H:27]([C:41]2[CH:46]=[CH:45][C:44]([Cl:47])=[C:43]([Cl:48])[CH:42]=2)[CH2:28][CH2:29][N:30]2[CH2:33][CH:32]([N:34]3[CH2:39][CH2:38][CH:37]([F:7])[CH2:36][CH2:35]3)[CH2:31]2)[CH3:25])=[O:23])[C:15]2[C:20]([CH:21]=1)=[CH:19][CH:18]=[CH:17][CH:16]=2)#[N:11]

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 11180534HCID 11180534, compound

Product 1

HCID 11478611HCID 11478611, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-65 °C

Procedure

Diethylaminosulfur trifluoride (7 mg, 0.044 mmol) was dissolved in dry CH2Cl2 and cooled with stirring under argon to −65° C. 3-Cyano-N-{(2S)-2-(3,4-dichlorophenyl)-4-[3-(4-oxopiperidin-1-yl)azetidin-1-yl]butyl}-N-methyl-1-naphthamide (Example 26; 40 mg, 0.071 mmol), which was dissolved in dry CH2Cl2 (0.5 mL), was then added. The external cooling was removed and the solution was stirred for 1 h. The reaction mixture was quenched by dropping it to a saturated solution of NaHCO3 aq. (6 mL). The organic solution was washed with water and then dried over MgSO4. The solvent was removed by evaporation and there was obtained 5 mg (12%) of the title compound as an oil. 1H NMR (500 MHz, CD3OD): 1.8-2.6 (cm, 7H), 2.6-3.3 (cm, 7H), 3.4-4.4 (cm, 9H), 5.0-5.3 (cm, 1H), 7.0-8.4 (cm, 7H), 8.4-8.6 (m, 1H), 8.9-9.0 (d, 1H); LCMS: m/z 567 (M+1)+.

Workup

  1. temperaturecooled
  2. additionwas then added
  3. temperatureThe external cooling
  4. customwas removed
  5. stirringthe solution was stirred for 1 h
  6. customThe reaction mixture was quenched
  7. washThe organic solution was washed with water
  8. dry with materialdried over MgSO4
  9. customThe solvent was removed by evaporation

Sources & evidence

ORD record
ord-584ab0316fb049339fe2298e9584cd0a
Source dataset
uspto-grants-2008_07
Patent number
US07402581B2

Reaction notes

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