Hydrochloric Acid → HCID 19707305, compound

HRID 726724Notes

Reaction equation

HRID 726724 reaction equation
[F:1][C:2]([F:33])([F:32])[C:3]1[CH:4]=[C:5]([CH:25]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:27]=1)[CH2:6][CH2:7][C:8]1[N:12]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:11](=[O:20])[N:10]([CH2:21][CH2:22][CH2:23][NH2:24])[N:9]=1.[NH:34]1[C:42]2[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=2)[C:36]([CH2:43][C:44](O)=[O:45])=[CH:35]1.CN(C)CCCN=C=NCC.Cl.OC1C2N=NNC=2C=CC=1.C(N(CC)CC)C>ClCCl.C(OCC)(=O)C>[F:33][C:2]([F:1])([F:32])[C:3]1[CH:4]=[C:5]([CH:25]=[C:26]([C:28]([F:30])([F:31])[F:29])[CH:27]=1)[CH2:6][CH2:7][C:8]1[N:12]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:11](=[O:20])[N:10]([CH2:21][CH2:22][CH2:23][NH:24][C:44](=[O:45])[CH2:43][C:36]2[C:37]3[C:42](=[CH:41][CH:40]=[CH:39][CH:38]=3)[NH:34][CH:35]=2)[N:9]=1

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 802Indole-3-Acetic AcidHCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 15295111HCID 15295111, compoundHCID 178418300HCID 178418300, compound

Product 1

HCID 19707305HCID 19707305, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-(3,5-Bis(trifluoromethyl)phenethyl)-4-benzyl-1-(3-aminopropyl)-5-oxo-1,2,4-triazole (Example 2, 0.500 g, 0.0010 mol) was dissolved in dichloromethane (20 ml) and indole-3-acetic acid (0.222 g, 0.00127 mol), 1-(3-dimethylamino-propyl)-3-ethylcarbodiimide.HCl (0.244 g, 0.00127 mol), hydroxybenzotriazole (0.171 g, 0.00127 mol) and triethylamine (0.7 ml, 0.005 mol) added. The reaction was stirred for 16 hours, diluted with ethyl acetate (50 ml), washed with 10% citric acid solution, saturated sodium bicarbonate solution and brine. The organic layer was dried (MgSO4) and solvent evaporated. The residue was chromatographed on silica eluting with ethyl acetate then 1% methanol/ethyl acetate, to give the title compound as a pale yellow solid (0.500 g 80%).

Workup

  1. washwashed with 10% citric acid solution, saturated sodium bicarbonate solution and brine
  2. dry with materialThe organic layer was dried (MgSO4) and solvent
  3. customevaporated
  4. customThe residue was chromatographed on silica eluting with ethyl acetate

Sources & evidence

ORD record
ord-5236ca59d97145d78fa852e865377475
Source dataset
uspto-grants-1998_01
Patent number
US05710161

Reaction notes

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