Triethylamine → HCID 67516346, compound

HRID 1801563Notes

Reaction equation

HRID 1801563 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, compound

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. 1H NMR (300 MHz, CDCl3/TMS) δ 7.31-7.05 (m, 6H), 6.96 (dd, J=13.6, 6.1 Hz, 1H), 6.87-6.71 (m, 2H), 6.30 (t, J=3.1 Hz, 0.5H), 6.25 (t, J=3.1 Hz, 0.5H), 6.07 (d, J=2.1 Hz, 0.5H), 5.88 (d, J=2.1 Hz, 0.5H), 5.52 (s, 1H), 4.28-4.03 (m, 3H), 3.91-3.68 (m, 2H), 3.48-3.12 (m, 2H), 3.10-2.96 (m, 1H), 2.12-1.78 (m, 2.5H), 1.68-1.54 (m, 2H), 1.44-1.36 (m, 0.5H). 13C NMR (75 MHz, CDCl3/TMS) 168.30, 133.82, 132.75, 132.61, 132.31, 132.18, 129.01, 127.24, 126.29, 125.68, 124.63, 119.64, 116.30, 114.50, 114.36, 109.91, 102.92, 102.61, 79.59, 79.39, 64.55, 51.36, 41.63, 41.50, 38.67, 36.30, 35.69, 35.52, 28.00.

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-98e221f24cae4214aaf1a4ff9a27ddfb
Source dataset
uspto-grants-2013_01
Patent number
US08349833B2

Reaction notes

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