Triethylamine → HCID 67516346, compound

HRID 1801569Notes

Reaction equation

HRID 1801569 reaction equation
C([N:3]([CH2:6][CH3:7])[CH2:4][CH3:5])C.[CH:8]1([C:18]([OH:20])=O)[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][CH2:10][O:9]1.F[P-](F)(F)(F)(F)F.[N:28]1(O[P+](N(C)C)(N(C)C)N(C)C)[C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=2[N:30]=N1>ClCCl>[CH:8]1([C:18]([N:3]2[CH2:4][CH2:5][C:14]3([NH:30][C:31]4[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=4)[N:28]4[CH:10]=[CH:11][CH:12]=[C:13]34)[CH2:7][CH2:6]2)=[O:20])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][CH2:10][O:9]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 3157295Isochroman-1-carboxylic acid

Product 1

HCID 67516346HCID 67516346, compoundYield 131.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4,5-dihydropyrrolo[1,2-a]quinoxaline-spiro-4-piperidine (2.0 mmol), triethylamine (2 mmol), isochroman-1-carboxylic acid (2 mmol) and Benzotriazole-1-yl-oxy-tris-(dimethylamino)-phosphonium hexafluorophosphate (2 mmol) in dichloromethane (10 mL) was stirred at room temperature for 16 hours. The mixture was quenched with saturated aqueous sodium bicarbonate solution (10 mL), stirred for 2 hours, and the product was extracted with dichloromethane (2×10 mL). The combined organic layers were dried over sodium sulfate and concentrated at reduced pressure to give a crude product. Purification via column chromatography (silica gel, ethyl acetate/hexane) afforded isochroman-1-yl(5′H-spiro[piperidine-4,4′-pyrrolo[1,2-a]quinoxaline]-1-yl)methanone (Compound VIIa, 527 mg, 66%).

Workup

  1. customThe mixture was quenched with saturated aqueous sodium bicarbonate solution (10 mL)
  2. stirringstirred for 2 hours
  3. extractionthe product was extracted with dichloromethane (2×10 mL)
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. concentrationconcentrated at reduced pressure
  6. customto give a crude product
  7. customPurification via column chromatography (silica gel, ethyl acetate/hexane)

Sources & evidence

ORD record
ord-d44a1fdba1ea4c1297b80fa4c0d8fa58
Source dataset
uspto-grants-2013_01
Patent number
US08349833B2

Reaction notes

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