Triethylamine → HCID 59175901, compound

HRID 1807727Notes

Reaction equation

HRID 1807727 reaction equation
[CH3:1][CH:2]([CH3:8])[CH2:3][CH2:4][C:5](Cl)=[O:6].[NH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([N:18]2[CH2:23][CH2:22][N:21]([CH2:24][C:25]3[CH:30]=[CH:29][C:28]([C:31]([OH:40])([C:36]([F:39])([F:38])[F:37])[C:32]([F:35])([F:34])[F:33])=[CH:27][CH:26]=3)[CH2:20][CH2:19]2)=[O:17])=[CH:12][C:11]=1[F:41].C(N(CC)CC)C>ClCCl>[F:41][C:11]1[CH:12]=[C:13]([C:16]([N:18]2[CH2:19][CH2:20][N:21]([CH2:24][C:25]3[CH:30]=[CH:29][C:28]([C:31]([OH:40])([C:32]([F:33])([F:34])[F:35])[C:36]([F:38])([F:39])[F:37])=[CH:27][CH:26]=3)[CH2:22][CH2:23]2)=[O:17])[CH:14]=[CH:15][C:10]=1[NH:9][C:5](=[O:6])[CH2:4][CH2:3][CH:2]([CH3:8])[CH3:1]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 170008Pentanoyl chloride, 4-methyl-HCID 86638550(4-Amino-3-fluorophenyl)(4-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)benzyl)piperazin-1-yl)methanone

Product 1

HCID 59175901HCID 59175901, compoundYield 9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Methylvaleric acid (4.30 mmol, 0.543 mL, 0.5 g) was stirred in dichloromethane (5 mL) at 0° C. Oxalyl chloride (21.52 mmol, 1.848 mL, 2.73 g) was added. The reaction mixture allowed to warm to room temperature and stirred for 18 hours. The reaction mixture was concentrated under vacuum to give the intermediate 4-methylpentanoyl chloride. A mixture of 4-methylpentanoyl chloride (1.564 mmol, 0.211 g), (4-amino-3-fluorophenyl)(4-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)benzyl)piperazin-1-yl)methanone (1.043 mmol, 0.5 g) and triethylamine (2.086 mmol, 0.290 mL, 0.211 g) were stirred in dichloromethane at 0° C. for 1 hour. The reaction mixture was washed with water, dried over sodium sulfate, concentrated under vacuum and purified by silica chromatography (eluting with a solvent gradient from dichloromethane to 5% methanol/dichloromethane) to afford the title compound (54 mg).

Workup

  1. washThe reaction mixture was washed with water
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated under vacuum
  4. custompurified by silica chromatography (
  5. washeluting with a solvent gradient from dichloromethane to 5% methanol/dichloromethane)

Sources & evidence

ORD record
ord-7fac6d7e33164767ba3f19de2d4df206
Source dataset
uspto-grants-2013_01
Patent number
US08357679B2

Reaction notes

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