Triethylamine → HCID 136348383, compound

HRID 869502Notes

Reaction equation

HRID 869502 reaction equation
[CH:1]1([C:4]2[N:5]=[C:6]3[CH:11]=[C:10]([C:12]([NH2:14])=O)[CH:9]=[CH:8][N:7]3[C:15]=2[CH2:16][C:17]2[CH:40]=[CH:39][C:20]3/[C:21](=[C:31](\[C:33]4[NH:37][C:36](=[O:38])[O:35][N:34]=4)/[CH3:32])/[C:22]4[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:23]=4[O:24][CH2:25][C:19]=3[CH:18]=2)[CH2:3][CH2:2]1.C(N(CC)CC)C.FC(F)(F)C(OC(=O)C(F)(F)F)=O.C(=O)([O-])O.[Na+]>C1COCC1>[CH:1]1([C:4]2[N:5]=[C:6]3[CH:11]=[C:10]([C:12]#[N:14])[CH:9]=[CH:8][N:7]3[C:15]=2[CH2:16][C:17]2[CH:40]=[CH:39][C:20]3/[C:21](=[C:31](\[C:33]4[NH:37][C:36](=[O:38])[O:35][N:34]=4)/[CH3:32])/[C:22]4[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:23]=4[O:24][CH2:25][C:19]=3[CH:18]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 516892Sodium BicarbonateHCID 136348384HCID 136348384, compound

Product 1

HCID 136348383HCID 136348383, compoundYield 52.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

[step 2] (E)-2-cyclopropyl-3-({3-fluoro-11(6H)-[1-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)ethylidene]dibenzo[b,e]oxepin-8-yl}methyl)imidazo[1,2-a]pyridine-7-carboxamide (83 mg, 0.15 mmol) obtained in step 1 was suspended in THF (0.77 mL), and triethylamine (0.11 mL, 0.77 mmol) was added. Under ice-cooling, trifluoroacetic anhydride (0.11 mL, 0.77 mmol) was added, and the mixture was stirred at room temperature for 4 hr. Saturated aqueous sodium hydrogen carbonate solution was added to the mixture, and the mixture was extracted 3 times with chloroform-methanol mixed solvent. The combined organic layers were dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol=100/0 v/v-90/10 v/v) to give the title compound (compound 14b) (41 mg, 51%).

Workup

  1. temperatureUnder ice-cooling
  2. extractionthe mixture was extracted 3 times with chloroform-methanol mixed solvent
  3. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (chloroform/methanol=100/0 v/v-90/10 v/v)

Sources & evidence

ORD record
ord-f063c3b15d854660b821e67a3540b124
Source dataset
uspto-grants-2015_03
Patent number
US08969345B2

Reaction notes

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