Triethylamine → HCID 59175893, compound

HRID 1807742Notes

Reaction equation

HRID 1807742 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 86638557HCID 86638557, compound

Product 1

HCID 59175893HCID 59175893, compoundYield 15.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(R)-1,1,1,3,3,3-Hexafluoro-2-(4-((3-methylpiperazin-1-yl)methyl)phenyl)propan-2-ol (0.427 mmol, 0.152 g), 4-(3-(cyclopropylmethyl)ureido)benzoic acid (0.427 mmol, 0.1 g) and triethylamine (1.281 mmol, 0.178 mL, 0.130 g) were combined in dichloromethane and stirred at room temperature. 1-Propanephosphonic acid cyclic anhydride (0.640 mmol, 0.381 mL, 0.407 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 (38 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-cb05457ccab8473aa2ca7a6780d6c980
Source dataset
uspto-grants-2013_01
Patent number
US08357679B2

Reaction notes

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