(Bis(2-methoxyethyl)amino)sulfur trifluoride → HCID 67974549, compound

HRID 1502389Notes

Reaction equation

HRID 1502389 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:26])=[C:6]([C:8]2[CH:17]=[C:16]3[C:11]([CH:12]=[C:13]([NH:18][C:19]([CH:21]4[CH2:23][CH2:22]4)=[O:20])[N:14]=[CH:15]3)=[C:10]([CH2:24]O)[N:9]=2)[CH:7]=1.COCCN(S(F)(F)[F:37])CCOC>ClCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:26])=[C:6]([C:8]2[CH:17]=[C:16]3[C:11]([CH:12]=[C:13]([NH:18][C:19]([CH:21]4[CH2:23][CH2:22]4)=[O:20])[N:14]=[CH:15]3)=[C:10]([CH2:24][F:37])[N:9]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 2734690(Bis(2-methoxyethyl)amino)sulfur trifluorideHCID 67974979HCID 67974979, compound

Product 1

HCID 67974549HCID 67974549, compoundYield 141.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a slurry of N-(7-(5-fluoro-2-methylphenyl)-5-(hydroxymethyl)-2,6-naphthyridin-3-yl)cyclopropanecarboxamide (60 mg, 0.1 mmol), in dichloromethane (0.7 mL) cooled at −15° C. was added bis(2-methoxyethyl)aminosulfur trifluoride (0.045 mL, 0.2 mmol). After 15 minutes at this temperature, the reaction mixture was diluted with dichlormethane (50 mL) and washed with water (20 mL). The organic layer was separated, dried over sodium sulfate, filtered, and evaporated in vacuo to afford a residue that was purified by reverse phase HPLC (5-85% acetonitrile in water with 0.1% formic acid over 14 min) to afford the title compound as an off-white solid (50 mg, 50%). 1H NMR (400 MHz, DMSO) δ 11.23 (s, 1H), 9.38 (s, 1H), 8.85 (s, 1H), 8.21 (s, 1H), 7.47-7.33 (m, 2H), 7.21 (m, 1H), 5.99 (s, 1H), 5.88 (s, 1H), 2.37 (s, 3H), 2.11 (m, 1H), 0.89 (m, 4H). LCMS (Method G): RT=14.65 min, M+H+=354.4.

Workup

  1. washwashed with water (20 mL)
  2. customThe organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customto afford a residue that
  7. customwas purified by reverse phase HPLC (5-85% acetonitrile in water with 0.1% formic acid over 14 min)

Sources & evidence

ORD record
ord-e89b0d701ef746c2a30ebbb93dda043b
Source dataset
uspto-grants-2015_12
Patent number
US09206175B2

Reaction notes

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