Triethylamine → HCID 86703766, compound

HRID 1849887Notes

Reaction equation

HRID 1849887 reaction equation
[F:1][C:2]1[C:3]([C:13]([O:15][CH3:16])=[O:14])=[CH:4][C:5]([I:12])=[C:6]([CH2:8][C:9]([OH:11])=O)[CH:7]=1.[CH:17]([N:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.Cl.CN(C)CCCN=C=NCC.N1C2C=CC=C(O)C=2N=N1.C(N(CC)CC)C>C(Cl)Cl>[CH:17]([N:30]1[CH2:35][CH2:34][N:33]([C:9](=[O:11])[CH2:8][C:6]2[C:5]([I:12])=[CH:4][C:3]([C:13]([O:15][CH3:16])=[O:14])=[C:2]([F:1])[CH:7]=2)[CH2:32][CH2:31]1)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 70048BenzhydrylpiperazineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86703767HCID 86703767, compoundHCID 178418300HCID 178418300, compound

Product 1

HCID 86703766HCID 86703766, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 2-(5-fluoro-2-iodo-4-(methoxycarbonyl)phenyl)acetic acid (100 mg, 0.30 mmol), 1-benzhydrylpiperazine (82 mg, 0.33 mmol), 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (86 mg, 0.45 mmol), 1H-benzo[d][1,2,3]triazol-4-ol (61 mg, 0.45 mmol) and triethylamine (91 mg, 0.90 mmol) in DCM (5.0 mL) was stirred at room temperature for 16 h. The mixture was diluted with DCM (20 mL), washed with HCl (2M, 10 mL) and brine (20 mL), dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by Combiflash (60%-70% CH3CN in 0.1% HCOOH) to afford methyl 4-(2-(4-benzhydrylpiperazin-1-yl)-2-oxoethyl)-2-fluoro-5-iodobenzoate (70 mg, 41%) as a white solid. LCMS (ESI): m/z: 572.8 [M+H]+.

Workup

  1. washwashed with HCl (2M, 10 mL) and brine (20 mL)
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by Combiflash (60%-70% CH3CN in 0.1% HCOOH)

Sources & evidence

ORD record
ord-0a3f5be4ebe44cbe9d2d05d0b7ee55df
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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