Triethylamine → HCID 57410108, compound

HRID 527686Notes

Reaction equation

HRID 527686 reaction equation
[CH3:1][C:2]([C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15]2[C:20]3[C:21]([CH3:24])=[N:22][O:23][C:19]=3[CH:18]=[CH:17][CH:16]=2)=[CH:10][CH:9]=1)=[O:6])([CH3:4])[NH2:3].C(N(CC)CC)C.Cl[C:33](Cl)([O:35]C(=O)OC(Cl)(Cl)Cl)Cl>C(OCC)(=O)C.CN(C1C=CN=CC=1)C>[CH3:4][C:2]1([CH3:1])[NH:3][C:33](=[O:35])[N:7]([C:8]2[CH:13]=[CH:12][C:11]([O:14][C:15]3[C:20]4[C:21]([CH3:24])=[N:22][O:23][C:19]=4[CH:18]=[CH:17][CH:16]=3)=[CH:10][CH:9]=2)[C:5]1=[O:6]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 67966943HCID 67966943, compound2×

Product 1

HCID 57410108HCID 57410108, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8857Ethyl AcetateSolvent2×

Procedure

2-methyl-N1-{4-[(3-methyl-1,2-benzisoxazol-4-yl)oxy]phenyl}alaninamide (Intermediate 25, 18 mg) was dissolved in 4 ml of ethyl acetate. Triethylamine (0.017 ml, 0.12 mmol) was then added followed by a solution of triphosgene (8.21 mg, 0.028 mmol) in 1.0 ml of ethyl acetate. After stirring for 5 minutes, DMAP (3.4 mg, 0.028 mmol) was added and the reaction mixture was stirred at room temperature for 10 minutes. After quenching with a saturated aqueous solution of NaHCO3, the mixture was extracted two times with ethyl acetate and the collected organic layers were dried over sodium sulphate, filtered and evaporated. The crude obtained was charged on a silica gel column and eluted with c-Hex/EtOAc as eluents (from all 100:0 to 0:100). This afforded 10 mg of the title compound.

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 10 minutes
  2. customAfter quenching with a saturated aqueous solution of NaHCO3
  3. extractionthe mixture was extracted two times with ethyl acetate
  4. dry with materialthe collected organic layers were dried over sodium sulphate
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude obtained
  8. additionwas charged on a silica gel column
  9. washeluted with c-Hex/EtOAc as eluents (from all 100:0 to 0:100)

Sources & evidence

ORD record
ord-297e26c81ba945ef8353bc70add02aac
Source dataset
uspto-grants-2016_05
Patent number
US09346790B2

Reaction notes

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