Triethylamine → HCID 16041744, compound

HRID 545169Notes

Reaction equation

HRID 545169 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:30](=[CH:31][CH:32]=1)[O:29][C:7]1([CH2:12][CH2:11][N:10]([C:13]([C:15]3[CH:24]=[C:23]([O:25][CH3:26])[C:22]4[C:17](=[C:18]([O:27][CH3:28])[CH:19]=[CH:20][CH:21]=4)[N:16]=3)=[O:14])[CH2:9][CH2:8]1)[CH2:6][C:5]2=[O:33].CC[N:36]([CH2:39]C)CC.ClC(OC1C=CC([N+]([O-])=O)=CC=1)=[O:43]>C1COCC1>[CH3:26][O:25][C:23]1[C:22]2[C:17](=[C:18]([O:27][CH3:28])[CH:19]=[CH:20][CH:21]=2)[N:16]=[C:15]([C:13]([N:10]2[CH2:11][CH2:12][C:7]3([CH2:6][C:5](=[O:33])[C:4]4[C:30](=[CH:31][CH:32]=[C:2]([NH:1][C:39]([NH2:36])=[O:43])[CH:3]=4)[O:29]3)[CH2:8][CH2:9]2)=[O:14])[CH:24]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 821294-Nitrophenyl chloroformateHCID 16041579HCID 16041579, compound

Product 1

HCID 16041744HCID 16041744, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The compound of Example 5 (1.35 g) was dissolved in 15 mL of THF; and 0.505 mL of NEt3 and 669 mg of 4-nitrophenyl chloroformate were added thereto in order, and stirred at room temperature. The reaction mixture was filtered, and 0.226 mL of 25% aqueous ammonia was added to the filtrate, and stirred overnight at room temperature. The reaction solution was diluted with chloroform, washed with water, dried over magnesium sulfate, and concentrated. The residue was purified through silica gel thin-layer chromatography (CHCl3/MeOH=7/1) to obtain the intended compound as a yellow amorphous solid. 1H-NMR (400 MHz, DMSO-d6) δ: 8.59 (1H, s), 7.80 (1H, d, J=2.9 Hz), 7.66 (1H, dd, J=8.5, 1.5 Hz), 7.53 (1H, dd, J=8.6, 3.0 Hz), 7.50 (1H, t, J=8.4 Hz), 7.22 (1H, dd, J=8.0, 2.0 Hz), 7.16 (1H, s), 6.99 (1H, d, J=8.8 Hz), 5.83 (2H, s), 4.21-4.36 (1H, m), 4.05 (3H, s), 3.93 (3H, s), 3.64-3.55 (1H, m), 3.46-3.32 (1H, m), 3.31-3.20 (1H, m), 2.84 (2H, s), 2.08-1.99 (1H, m), 1.91-1.84 (1H, m), 1.83-1.70 (2H, m). MS [M+H]+=491.

Workup

  1. filtrationThe reaction mixture was filtered
  2. addition0.226 mL of 25% aqueous ammonia was added to the filtrate
  3. stirringstirred overnight at room temperature
  4. additionThe reaction solution was diluted with chloroform
  5. washwashed with water
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated
  8. customThe residue was purified through silica gel thin-layer chromatography (CHCl3/MeOH=7/1)

Sources & evidence

ORD record
ord-a4002877ab41487981c6eaccedfbe51a
Source dataset
uspto-grants-2011_05
Patent number
US07935712B2

Reaction notes

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