(Bis(2-methoxyethyl)amino)sulfur trifluoride → HCID 178455692, compound

HRID 237342Notes

Reaction equation

HRID 237342 reaction equation
[Cl:1][C:2]1[CH:27]=[CH:26][C:5]2[N:6]3[C:10]([CH2:11][N:12]([CH3:14])[CH2:13][C:4]=2[CH:3]=1)=[N:9][N:8]=[C:7]3[C@H:15]1[CH2:20][CH2:19][C@H:18]([O:21][CH:22]([CH3:25])[CH2:23]O)[CH2:17][CH2:16]1.COCCN(S(F)(F)[F:38])CCOC>ClCCl>[Cl:1][C:2]1[CH:27]=[CH:26][C:5]2[N:6]3[C:10]([CH2:11][N:12]([CH3:14])[CH2:13][C:4]=2[CH:3]=1)=[N:9][N:8]=[C:7]3[C@H:15]1[CH2:20][CH2:19][C@H:18]([O:21][CH:22]([CH3:25])[CH2:23][F:38])[CH2:17][CH2:16]1

Participants

4

Reactant 2

HCID 2734690(Bis(2-methoxyethyl)amino)sulfur trifluoride2×HCID 178460518HCID 178460518, compound

Product 1

HCID 178455692HCID 178455692, compoundYield 36.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (RS)-trans-2-[4-(8-chloro-5-methyl-5,6-dihydro-4H-2,3,5,10b-tetraaza-benzo[e]azulen-1-yl)-cyclohexyloxy]-propan-1-ol (0.055 g, 0.14 mmol) in dichloromethane (2 ml) was added [bis(2-methoxyethyl)-amino]sulfur trifluoride (0.031 ml, 0.17 mmol) at 0-5° C. Stirring at room temperature for 18 h was followed by addition of further [bis(2-methoxyethyl)-amino]sulfur trifluoride (0.016 ml, 0.08 mmol) and stirring for 4 h. The reaction mixture was partitioned between saturated aqueous sodium bicarbonate solution (30 ml) and ethyl acetate (30 ml). The layers were separated and the aqueous layer was extracted with two 30-ml portions of ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate and concentrated in vacuo. Flash-chromatography with n-heptane/2-propanol as eluent gave the title compound (0.020 g, 36%) as white solid. MS m/e: 393 (M+H+).

Workup

  1. stirringstirring for 4 h
  2. customThe reaction mixture was partitioned between saturated aqueous sodium bicarbonate solution (30 ml) and ethyl acetate (30 ml)
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with two 30-ml portions of ethyl acetate
  5. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-48e9e575bb244185bdc46e15d138758c
Source dataset
uspto-grants-2014_02
Patent number
US08642590B2

Reaction notes

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