Triethylamine → HCID 89610367, compound

HRID 1507701Notes

Reaction equation

HRID 1507701 reaction equation
[CH2:1]([O:8][C:9]1[C:13]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:12]([C:22]([NH2:24])=O)[N:11]([C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=2)[C:10]=1[C:33]([NH2:35])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[NH4+].C(N(CC)CC)C.FC(F)(F)C(OC(=O)C(F)(F)F)=O>C(Cl)Cl>[CH2:15]([O:14][C:13]1[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[C:10]([C:33]#[N:35])[N:11]([C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=2)[C:12]=1[C:22]#[N:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 25517Ammonium ChlorideHCID 71599885HCID 71599885, compound

Product 1

HCID 89610367HCID 89610367, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 3,4-bis(benzyloxy)-1-(4-methoxyphenyl)-1H-pyrrole-2,5-dicarboxamide (13) [prepared using the same procedure as Example A step (ii) using ammonium chloride] (267 mg, 0.57 mmol) and triethylamine (710 μL, 5.10 mmol) in DCM (8 mL) at 0° C. was added trifluoroacetic anhydride (240 μL, 1.70 mmol) and the reaction allowed to warm to RT over 30 min. The reaction mixture was partitioned between DCM (50 mL) and 1 M HCl (aq.) (30 mL), the organic was washed with 1 M HCl (aq.) (20 mL), sat. NaHCO3 (aq.) (30 mL), and brine (20 mL), dried (MgSO4), filtered and volatiles removed in vacuo to afford a yellow solid. The crude residue was purified by silica gel chromatography (40 g, 0-50% EtOAc in isohexane) to afford 3,4-bis(benzyloxy)-1-(4-methoxyphenyl)-1H-pyrrole-2,5-dicarbonitrile (14) (240 mg, 97%) as a pale yellow solid: 1H NMR (400 MHz, DMSO-d6) δ: 7.47-7.27 (m, 10H), 7.30-7.20 (m, 2H), 7.05-6.91 (m, 2H), 5.26 (s, 4H), 3.79 (s, 3H).

Workup

  1. customat 0° C.
  2. customThe reaction mixture was partitioned between DCM (50 mL) and 1 M HCl (aq.) (30 mL)
  3. washthe organic was washed with 1 M HCl (aq.) (20 mL), sat. NaHCO3 (aq.) (30 mL), and brine (20 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customvolatiles removed in vacuo
  7. customto afford a yellow solid
  8. customThe crude residue was purified by silica gel chromatography (40 g, 0-50% EtOAc in isohexane)

Sources & evidence

ORD record
ord-c473b321f5b541eb98410bee1355e940
Source dataset
uspto-grants-2015_12
Patent number
US09221756B2

Reaction notes

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