Triethylamine → HCID 59175836, compound

HRID 1807744Notes

Reaction equation

HRID 1807744 reaction equation
[F:1][C:2]([F:24])([F:23])[C:3]([C:9]1[CH:14]=[CH:13][C:12]([CH2:15][N:16]2[CH2:21][CH2:20][NH:19][C@@H:18]([CH3:22])[CH2:17]2)=[CH:11][CH:10]=1)([OH:8])[C:4]([F:7])([F:6])[F:5].[CH:25]1([CH2:28][NH:29][C:30](=[O:41])[NH:31][C:32]2[CH:40]=[CH:39][C:35]([C:36](O)=[O:37])=[CH:34][CH:33]=2)[CH2:27][CH2:26]1.C(N(CC)CC)C.CCCP1(OP(CCC)(=O)OP(CCC)(=O)O1)=O>ClCCl>[CH:25]1([CH2:28][NH:29][C:30]([NH:31][C:32]2[CH:33]=[CH:34][C:35]([C:36]([N:19]3[CH2:20][CH2:21][N:16]([CH2:15][C:12]4[CH:11]=[CH:10][C:9]([C:3]([OH:8])([C:4]([F:7])([F:6])[F:5])[C:2]([F:23])([F:1])[F:24])=[CH:14][CH:13]=4)[CH2:17][C@@H:18]3[CH3:22])=[O:37])=[CH:39][CH:40]=2)=[O:41])[CH2:27][CH2:26]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 111923Propylphosphonic anhydrideHCID 580558194-(3-(Cyclopropylmethyl)ureido)benzoic acidHCID 86638558HCID 86638558, compound

Product 1

HCID 59175836HCID 59175836, compoundYield 6.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-1,1,1,3,3,3-Hexafluoro-2-(4-((3-methylpiperazin-1-yl)methyl)phenyl)propan-2-ol (0.854 mmol, 0.304 g), 4-(3-(cyclopropylmethyl)ureido)benzoic acid (0.854 mmol, 0.2 g) and triethylamine (2.56 mmol, 0.356 mL, 0.259 g) were combined in dichloromethane and stirred at room temperature. 1-Propanephosphonic acid cyclic anhydride (1.28 mmol, 0.762 mL, 0.815 g; 50% solution in ethyl acetate) was added and the reaction allowed to stir for 1 hour. The reaction mixture was washed with saturated sodium bicarbonate solution, dried over sodium sulfate and concentrated under vacuum. The resulting residue was purified by silica chromatography (eluting with a solvent gradient from dichloromethane to 5% methanol/dichloromethane) to afford the title compound (32 mg).

Workup

  1. stirringto stir for 1 hour
  2. washThe reaction mixture was washed with saturated sodium bicarbonate solution
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under vacuum
  5. customThe resulting residue was purified by silica chromatography (
  6. washeluting with a solvent gradient from dichloromethane to 5% methanol/dichloromethane)

Sources & evidence

ORD record
ord-cbd859e84b9d4cd99fe474aa5ae00bd7
Source dataset
uspto-grants-2013_01
Patent number
US08357679B2

Reaction notes

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