Triethylamine → 1-[3-[(N-Ethylpyrrolidin-2-ylmethyl)carbamoyl]phenyl carbamoyl]-5-methylthio-6-trifluoromethyl indoline

HRID 1740810Notes

Reaction equation

HRID 1740810 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.[CH2:41]([N:43]1[CH2:47][CH2:46][CH2:45][CH:44]1[CH2:48][NH2:49])[CH3:42]>ClCCl.C1COCC1.CN(C=O)C>[CH2:41]([N:43]1[CH2:47][CH2:46][CH2:45][CH:44]1[CH2:48][NH:49][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])[CH3:42]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 1172952-Aminomethyl-1-ethylpyrrolidineHCID 180051075-Methylthio-6-trifluoromethyl-1-(3-carboxy Phenyl Carbamoyl)indoline

Product 1

HCID 218331101-[3-[(N-Ethylpyrrolidin-2-ylmethyl)carbamoyl]phenyl carbamoyl]-5-methylthio-6-trifluoromethyl indoline

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

The carboxylic acid from Example 12 (0.5 g, 1.25 mol) in dichloromethane (10 ml) was treated with oxalyl chloride (6.3 ml, 3.4 mmol) and DMF (catalytic). The solution was stirred for 1 hour 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-Ethyl-2-aminomethyl pyrrolidine (0.57 g, 4.5 mmol). After 3 hours at room temperature the solution was partitioned (EtOAc/H2O). Drying and removal of organics followed by rexst (EtOAc/60°-80° C. petrol) afforded the title compound as a white powder, m.pt. 174°-175° C.

Workup

  1. customevaporated to dryness
  2. customAfter 3 hours at room temperature the solution was partitioned (EtOAc/H2O)
  3. customDrying
  4. customremoval
  5. customof organics followed by rexst (EtOAc/60°-80° C. petrol)

Sources & evidence

ORD record
ord-e5e91b3376fa42d481c7301bb084e620
Source dataset
uspto-grants-1999_10
Patent number
US05972937

Reaction notes

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