(Bis(2-methoxyethyl)amino)sulfur trifluoride → HCID 86711560, compound

HRID 512515Notes

Reaction equation

HRID 512515 reaction equation
[CH3:1][NH:2][C:3]([C:5]1[C:10](=[O:11])[C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18]O)[CH:13]=2)=[C:8]([CH3:20])[N:7]([CH:21]([C:23]2[CH:28]=[CH:27][C:26]([C:29]#[N:30])=[CH:25][CH:24]=2)[CH3:22])[CH:6]=1)=[O:4].COCCN(S(F)(F)[F:41])CCOC>ClCCl>[CH3:1][NH:2][C:3]([C:5]1[C:10](=[O:11])[C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][F:41])[CH:13]=2)=[C:8]([CH3:20])[N:7]([CH:21]([C:23]2[CH:28]=[CH:27][C:26]([C:29]#[N:30])=[CH:25][CH:24]=2)[CH3:22])[CH:6]=1)=[O:4]

Participants

4

Reactant 2

HCID 2734690(Bis(2-methoxyethyl)amino)sulfur trifluorideHCID 86711561HCID 86711561, compound

Product 1

HCID 86711560HCID 86711560, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of preparation 31a (60 mg, 149 μmol) and [bis(2-methoxyethyl)amino]sulfur trifluoride (50% in toluene, 74 μL, 202 μmol) in dichloromethane (1 mL) is stirred for 3 h at room temperature. The reaction mixture is quenched with 1N HCl, extracted twice with dichloromethane and the organic phase is concentrated under reduced pressure. The remaining residue is purified by preparative reversed-phase HPLC (Stable Bond, gradient of acetonitrile in water, 0.1% TFA, 60° C.). Yield: 30 mg (50% of theory); ESI mass spectrum: [M+H]+=404; Retention time HPLC: 0.95 min (Z017—504).

Workup

  1. customThe reaction mixture is quenched with 1N HCl
  2. extractionextracted twice with dichloromethane
  3. concentrationthe organic phase is concentrated under reduced pressure
  4. customThe remaining residue is purified by preparative reversed-phase HPLC (Stable Bond, gradient of acetonitrile in water, 0.1% TFA, 60° C.)
  5. custom0.95 min (Z017—504)

Sources & evidence

ORD record
ord-bc709a6f689141abb54165612a0b8d40
Source dataset
uspto-grants-2015_08
Patent number
US09102624B2

Reaction notes

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