Triethylamine → HCID 24804922, compound

HRID 2197445Notes

Reaction equation

HRID 2197445 reaction equation
ClC(Cl)(O[C:5](=[O:11])OC(Cl)(Cl)Cl)Cl.Cl.[S:14]1[CH:18]=[CH:17][CH:16]=[C:15]1[C:19]1[N:23]=[C:22]([CH:24]2[CH2:29][CH2:28][NH2+:27][CH2:26][CH2:25]2)[O:21][N:20]=1.C(N(CC)CC)C.[CH:37]1([NH2:40])[CH2:39][CH2:38]1>C1(C)C=CC=CC=1.ClCCl>[CH:37]1([NH:40][C:5]([N:27]2[CH2:28][CH2:29][CH:24]([C:22]3[O:21][N:20]=[C:19]([C:15]4[S:14][CH:18]=[CH:17][CH:16]=4)[N:23]=3)[CH2:25][CH2:26]2)=[O:11])[CH2:39][CH2:38]1

Participants

7

Reactant 4

HCID 8471Triethylamine2×HCID 69828CyclopropylamineHCID 94429TriphosgeneHCID 86654171HCID 86654171, compound

Product 1

HCID 24804922HCID 24804922, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

54.60 mg (1 eq.) of triphosgene were added to a suspension of 150 mg (3 eq.) of 4-(3-thiophen-2-yl[1,2,4]oxadiazol-5-yl)piperidinium hydrochloride and 102.63 μl (4 eq.) of triethylamine in 2 ml of toluene. The reaction medium was stirred overnight at room temperature and then filtered. The filtrate thus collected was concentrated under reduced pressure. The residue obtained was taken up in 2 ml of dichloromethane, followed by addition of 77 μL (1 eq.) of triethylamine and 77.44 μl (2 eq.) of cyclopropylamine. The reaction medium was stirred for 20 hours at room temperature and then concentrated to dryness. The residue was chromatograph on a thick layer of silica (eluent: CH2Cl2/MeOH (95/5; v/v)) to give 80 mg (45%) of the expected product.

Workup

  1. filtrationfiltered
  2. customThe filtrate thus collected
  3. concentrationwas concentrated under reduced pressure
  4. customThe residue obtained
  5. stirringThe reaction medium was stirred for 20 hours at room temperature
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-9f2f61f18df649e69c958229f27dee8e
Source dataset
uspto-grants-2012_12
Patent number
US08338599B2

Reaction notes

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