Triethylamine → HCID 59175841, compound

HRID 1807746Notes

Reaction equation

HRID 1807746 reaction equation
[CH3:1][C@H:2]1[NH:7][C@@H:6]([CH3:8])[CH2:5][N:4]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]([OH:25])([C:21]([F:24])([F:23])[F:22])[C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=2)[CH2:3]1.[CH:26]1([CH2:29][NH:30][C:31](=[O:42])[NH:32][C:33]2[CH:41]=[CH:40][C:36]([C:37](O)=[O:38])=[CH:35][CH:34]=2)[CH2:28][CH2:27]1.C(N(CC)CC)C.CCCP1(OP(CCC)(=O)OP(CCC)(=O)O1)=O>ClCCl>[CH:26]1([CH2:29][NH:30][C:31]([NH:32][C:33]2[CH:34]=[CH:35][C:36]([C:37]([N:7]3[C@H:6]([CH3:8])[CH2:5][N:4]([CH2:9][C:10]4[CH:11]=[CH:12][C:13]([C:16]([OH:25])([C:21]([F:24])([F:23])[F:22])[C:17]([F:18])([F:19])[F:20])=[CH:14][CH:15]=4)[CH2:3][C@@H:2]3[CH3:1])=[O:38])=[CH:40][CH:41]=2)=[O:42])[CH2:28][CH2:27]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 111923Propylphosphonic anhydrideHCID 580558194-(3-(Cyclopropylmethyl)ureido)benzoic acidHCID 86638559HCID 86638559, compound

Product 1

HCID 59175841HCID 59175841, compoundYield 1.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(4-((-3,5-cis-Dimethylpiperazin-1-yl)methyl)phenyl)-1,1,1,3,3,3-hexafluoro-propan-2-ol (0.27 mmol, 0.1 g), 4-(3-(cyclopropylmethyl)ureido)benzoic acid (0.27 mmol, 0.063 g) and triethylamine (0.81 mmol, 0.113 mL, 0.082 g) were combined in dichloromethane and stirred at room temperature. 1-Propanephosphonic acid cyclic anhydride (0.405 mmol, 0.241 mL, 0.258 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 acidic preparative HPLC to afford the desired compound (3 mg). MS (ESI) m/z 587.3 [M+H]+

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 acidic preparative HPLC

Sources & evidence

ORD record
ord-f0cdf6a7736a402a80a334b878b05918
Source dataset
uspto-grants-2013_01
Patent number
US08357679B2

Reaction notes

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