Triethylamine → HCID 86638572, compound

HRID 1807783Notes

Reaction equation

HRID 1807783 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[F:11].[F:12][C:13]([F:35])([F:34])[C:14]([C:20]1[CH:33]=[CH:32][C:23]([CH2:24][N:25]2[CH2:30][CH2:29][NH:28][CH2:27][C:26]2=[O:31])=[CH:22][CH:21]=1)([OH:19])[C:15]([F:18])([F:17])[F:16].C(N(CC)CC)C.CCCP1(OP(CCC)(=O)OP(CCC)(=O)O1)=O>ClCCl>[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([N:28]2[CH2:29][CH2:30][N:25]([CH2:24][C:23]3[CH:32]=[CH:33][C:20]([C:14]([OH:19])([C:13]([F:12])([F:34])[F:35])[C:15]([F:18])([F:16])[F:17])=[CH:21][CH:22]=3)[C:26](=[O:31])[CH2:27]2)=[O:8])=[CH:4][C:3]=1[F:11]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 99714-Amino-3-fluorobenzoic acidHCID 111923Propylphosphonic anhydrideHCID 86638571HCID 86638571, compound

Product 1

HCID 86638572HCID 86638572, compoundYield 56.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirring solution of 4-amino-3-fluorobenzoic acid (1.965 mmol, 305 mg), 1-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)benzyl)piperazin-2-one (1.965 mmol, 700 mg) and triethylamine (5.89 mmol, 596 mg) in dichloromethane (10 mL) was added 1-propanephosphonic acid cyclic anhydride (2.95 mmol, 1876 mg; 50% solution in ethyl acetate). The reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was diluted with dichloromethane (20 mL) and washed with saturated aqueous sodium hydrogen carbonate solution (30 mL). The organic phase was concentrated and the resulting residue was purified by column chromatography on silica gel (eluting with 50% ethyl acetate/50% dichloromethane—100% ethyl acetate gradient) to afford the title compound (550 mg). MS (ESI) m/z 492.3 [M−H]−

Workup

  1. washwashed with saturated aqueous sodium hydrogen carbonate solution (30 mL)
  2. concentrationThe organic phase was concentrated
  3. customthe resulting residue was purified by column chromatography on silica gel (eluting with 50% ethyl acetate/50% dichloromethane—100% ethyl acetate gradient)

Sources & evidence

ORD record
ord-24381c991c9b4fd18719b1c5e1e80714
Source dataset
uspto-grants-2013_01
Patent number
US08357679B2

Reaction notes

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