Ammonium Sulfate → HCID 23435579, compound

HRID 2120733Notes

Reaction equation

HRID 2120733 reaction equation
C1C2C(COC([N:18]3[C:23]4[CH:24]=[CH:25][C:26]([C:28]5[NH:29][C:30]([C:33]#[N:34])=[CH:31][CH:32]=5)=[CH:27][C:22]=4[C:21]([CH3:36])([CH3:35])[O:20][CH:19]3[CH3:37])=O)C3C(=CC=CC=3)C=2C=CC=1.S([O-])([O-])(=O)=O.[NH4+].[NH4+]>N1CCCCC1.CN(C=O)C>[CH3:37][CH:19]1[O:20][C:21]([CH3:36])([CH3:35])[C:22]2[CH:27]=[C:26]([C:28]3[NH:29][C:30]([C:33]#[N:34])=[CH:31][CH:32]=3)[CH:25]=[CH:24][C:23]=2[NH:18]1

Participants

5

Reactant 2

HCID 6097028Ammonium SulfateHCID 23435592HCID 23435592, compound

Product 1

HCID 23435579HCID 23435579, compoundYield 56.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8082PiperidineSolvent

Procedure

A solution of 9H-fluoren-9-ylmethyl-6-[5-cyano-1H-pyrrol-2-yl]-2,4,4-trimethyl-2H-3,1-benzoxazine-1 (4H)-carboxylate (0.1 g, 0.2 mmol) in 20% piperidine in DMF (5 mL) was stirred at room temperature under nitrogen for 10 minutes. The mixture was poured into a saturated ammonium sulfate solution (30 mL) and extracted with diethyl ether (3×30 mL). The combined organic layers were dried (MgSO4) and evaporated. The residue was purified by a silica gel column chromatography (hexane:ethyl acetate/3:1) to afford the title compound as a white solid (0.03 g, 56%): mp 201-202° C.; 1H-NMR (DMSO-d6) δ 12.27 (s, 1H), 7.44 (d, 1H, J=2.1 Hz), 7.32 (dd, 1H, J=8.3, 1.1 Hz), 6.92 (dd, 1H, J=4.1, 2.6 Hz), 6.57 (d, 1H, J=8.3 Hz), 6.50 (dd, 1H, J=4.2, 2.6 Hz), 6.40 (s, 1H), 4.77-4.80 (m, 1H), 1.51 (s, 3H), 1.46 (s, 3H), 1.27 (d, 3H, J=5.7 Hz); MS (ESI) m/z 266 [M−H]−.

Workup

  1. extractionextracted with diethyl ether (3×30 mL)
  2. dry with materialThe combined organic layers were dried (MgSO4)
  3. customevaporated
  4. customThe residue was purified by a silica gel column chromatography (hexane:ethyl acetate/3:1)

Sources & evidence

ORD record
ord-b34222ccd5384054a5ebd50f15c50238
Source dataset
uspto-grants-2004_02
Patent number
US06693103B2

Reaction notes

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