Triethylamine → HCID 54137663, compound

HRID 1740809Notes

Reaction equation

HRID 1740809 reaction equation
[CH3:1][S:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[C:12]([F:15])([F:14])[F:13])[N:8]([C:16](=[O:27])[NH:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([C:24](O)=[O:25])[CH:19]=1)[CH2:7][CH2:6]2.C(Cl)(=O)C(Cl)=O.C(N(CC)CC)C.[CH3:41][N:42]([CH3:47])[CH2:43][CH2:44][NH:45][CH3:46]>ClCCl.C1COCC1.CN(C=O)C>[CH3:41][N:42]([CH3:47])[CH2:43][CH2:44][N:45]([CH3:46])[C:24]([C:20]1[CH:19]=[C:18]([NH:17][C:16]([N:8]2[C:9]3[C:5](=[CH:4][C:3]([S:2][CH3:1])=[C:11]([C:12]([F:13])([F:15])[F:14])[CH:10]=3)[CH2:6][CH2:7]2)=[O:27])[CH:23]=[CH:22][CH:21]=1)=[O:25]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 673381,2-Ethanediamine, N1,N1,N2-trimethyl-HCID 180051075-Methylthio-6-trifluoromethyl-1-(3-carboxy Phenyl Carbamoyl)indoline

Product 1

HCID 54137663HCID 54137663, compoundYield 83.2%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

The carboxylic acid from Example 12 (0.5 g, 1.25 mmol) in dichloromethane (10 ml) was treated with oxalyl chloride (0.3 ml, 3.4 mol) and DMF (catalytic). Solution was stirred for 1 h and evaporated to dryness. The residue in dry THF (5 ml) was added to a stirred solution of triethylamine (0.3 ml, 4 mmol) and N,N,N'-trimethylethylenediamine (0.5 ml, 4.5 mmol) in dry THF (10 ml). Following 3 hours at room temperature, the solution was partitioned (H2O/EtOAc). Drying and removal of the organic layers followed by recrystallisation (EtOAc/60°-80° petrol) afforded the title compound (0.5 g, 83%) as a white solid. M.pt. 140°-141° C.

Workup

  1. customevaporated to dryness
  2. waitFollowing 3 hours at room temperature
  3. customthe solution was partitioned (H2O/EtOAc)
  4. customDrying
  5. customremoval of the organic layers
  6. customfollowed by recrystallisation (EtOAc/60°-80° petrol)

Sources & evidence

ORD record
ord-358a48d0a59041da99095b831ed2776a
Source dataset
uspto-grants-1999_10
Patent number
US05972937

Reaction notes

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