Triethylamine → HCID 73703361, compound

HRID 2307467Notes

Reaction equation

HRID 2307467 reaction equation
[F:1][C:2]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:3]=1[CH:4]=[CH:5][C:6]([OH:8])=O.[NH2:14][CH:15]([C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[N:22]([C:26]([O:28][CH3:29])=[O:27])[CH2:21][CH2:20]2)[CH3:16].CCN=C=NCCCN(C)C.Cl.C(N(CC)CC)C>CN(C1C=CN=CC=1)C.C(Cl)Cl.O>[F:1][C:2]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:3]=1[CH:4]=[CH:5][C:6]([NH:14][CH:15]([C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[N:22]([C:26]([O:28][CH3:29])=[O:27])[CH2:21][CH2:20]2)[CH3:16])=[O:8]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 6035023-(2,4-Difluorophenyl)acrylic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 20744324HCID 20744324, compound

Product 1

HCID 73703361HCID 73703361, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 2,4-difluorocinnamic acid (0.5 mmol), (±)-5-(1-aminoethyl)-2,3-dihydro-indole-1-carboxylic acid, methyl ester, Preparation 20 (132 mg, 0.6 mmole), EDC hydrochloride (192 mg, 1.0 mmole), DMAP (61 mg, 0.5 mmole), and triethylamine (202 mg, 2 mmole) in CH2Cl2 (8 mL) was stirred at room temperature for 16 hours. Water was added, the aqueous layer was extracted with dichloromethane, and the combined organic layers were washed with brine, dried over magnesium sulfate, and evaporated in vacuo. The crude product was purified by flash column chromatography on silica eluting with EtOAc/hexane (7:3) to give the title compound (125 mg) as a solid.

Workup

  1. extractionthe aqueous layer was extracted with dichloromethane
  2. washthe combined organic layers were washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe crude product was purified by flash column chromatography on silica eluting with EtOAc/hexane (7:3)

Sources & evidence

ORD record
ord-d1f975ccace542029cab822285812264
Source dataset
uspto-grants-2004_12
Patent number
US06831080B2

Reaction notes

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