Ethylamine → HCID 58086682, compound

HRID 1098425Notes

Reaction equation

HRID 1098425 reaction equation
[F:1][C:2]1[C:21]([NH:22][S:23]([CH2:26][CH2:27][CH3:28])(=[O:25])=[O:24])=[CH:20][CH:19]=[C:18]([F:29])[C:3]=1[C:4]([C:6]1[C:14]2[C:9](=[N:10][CH:11]=[C:12]([C:15](O)=[O:16])[CH:13]=2)[NH:8][CH:7]=1)=[O:5].[CH2:30]([NH2:32])[CH3:31].F[P-](F)(F)(F)(F)F.Br[P+](N1CCCC1)(N1CCCC1)N1CCCC1.C(N(CC)CC)C>O1CCCC1.O>[CH2:30]([NH:32][C:15]([C:12]1[CH:13]=[C:14]2[C:6]([C:4](=[O:5])[C:3]3[C:18]([F:29])=[CH:19][CH:20]=[C:21]([NH:22][S:23]([CH2:26][CH2:27][CH3:28])(=[O:24])=[O:25])[C:2]=3[F:1])=[CH:7][NH:8][C:9]2=[N:10][CH:11]=1)=[O:16])[CH3:31]

Participants

7

Reactant 4

HCID 6341EthylamineHCID 8471TriethylamineHCID 2733179PyBroPHCID 58087848HCID 58087848, compound

Product 1

HCID 58086682HCID 58086682, compoundYield 33%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 3-[2,6-difluoro-3-(propane-1-sulfonylamino)-benzoyl]-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid (P-1559, 38.0 mg, 0.090 mmol) in tetrahydrofuran (2.3 mL) was added a solution of ethylamine (2.0 M in tetrahydrofuran, 0.20 mL), bromo-tris-pyrrolidino-phosphonium hexafluorophosphate (80.0 mg, 0.17 mmol) and triethylamine (0.30 mL, 2.2 mmol) under an atmosphere of nitrogen. The reaction mixture was stirred overnight at room temperature. The reaction was poured into water and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated and purified by silica gel column chromatography eluting with 40% ethyl acetate in hexane to give the compound as a white solid (P-1630, 13.2 mg, 33%). MS (ESI) [M−H+]−=449.0.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. custompurified by silica gel column chromatography
  6. washeluting with 40% ethyl acetate in hexane

Sources & evidence

ORD record
ord-09dd243d5ce840e79e8ba104fdb4893e
Source dataset
uspto-grants-2012_03
Patent number
US08143271B2

Reaction notes

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