Triethylamine → HCID 67353772, compound

HRID 1045518Notes

Reaction equation

HRID 1045518 reaction equation
FC(F)(F)C(O)=O.[NH2:8][C:9]1([C:21]([NH2:23])=[O:22])[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([N+:18]([O-:20])=[O:19])[CH:15]=2)[CH2:10]1.[CH3:24][C:25]([CH3:30])([CH3:29])[C:26](Cl)=[O:27].C(N(CC)CC)C.[NH4+].[Cl-]>C1COCC1>[CH3:24][C:25]([CH3:30])([CH3:29])[C:26]([NH:8][C:9]1([C:21]([NH2:23])=[O:22])[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([N+:18]([O-:20])=[O:19])[CH:15]=2)[CH2:10]1)=[O:27]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 62493Pivaloyl chlorideHCID 67376497HCID 67376497, compound2×

Product 1

HCID 67353772HCID 67353772, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (±)-2-amino-5-nitroindane-2-carboxamide, trifluoroacetate salt (described in Intermediate 3, 25.0 mg, 0.075 mmol), 2,2-dimethylpropanoyl chloride (0.011 mL, 0.089 mmol), and triethylamine (0.026 mL, 0.186 mmol) in THF (5 mL) was stirred at ambient temperature for 16 h. The reaction mixture was poured onto saturated NH4Cl (10 mL) and extracted with CH2Cl2 (3×10 mL). A solid precipitate was filtered and collected, then dissolved in MeOH and combined with the organic layers. The combined organic layers were dried over Na2SO4, filtered, and concentrated under reduced pressure to give the title compound. MS: m/z=306 (M+1).

Workup

  1. extractionextracted with CH2Cl2 (3×10 mL)
  2. filtrationA solid precipitate was filtered
  3. customcollected
  4. dissolutiondissolved in MeOH
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-65b07628a2a04fc0a0f388ef3bc3c90d
Source dataset
uspto-grants-2013_10
Patent number
US08569291B2

Reaction notes

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