4-Amino-3-fluorobenzoic acid → HCID 57917595, compound

HRID 1878400Notes

Reaction equation

HRID 1878400 reaction equation
[C:1]([NH:5][C:6](=[O:23])[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH:13]([N:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)[CH:14]([CH3:16])[CH3:15])[CH:8]=1)([CH3:4])([CH3:3])[CH3:2].[NH2:24][C:25]1[CH:33]=[CH:32][C:28]([C:29](O)=[O:30])=[CH:27][C:26]=1[F:34].C(N(C(C)C)C(C)C)C.CCCP1(OP(CCC)(=O)OP(CCC)(=O)O1)=O>ClCCl>[NH2:24][C:25]1[CH:33]=[CH:32][C:28]([C:29]([N:20]2[CH2:19][CH2:18][N:17]([CH:13]([C:9]3[CH:8]=[C:7]([CH:12]=[CH:11][CH:10]=3)[C:6]([NH:5][C:1]([CH3:3])([CH3:4])[CH3:2])=[O:23])[CH:14]([CH3:16])[CH3:15])[CH2:22][CH2:21]2)=[O:30])=[CH:27][C:26]=1[F:34]

Participants

6

Reactant 4

HCID 99714-Amino-3-fluorobenzoic acidHCID 81531DiisopropylethylamineHCID 111923Propylphosphonic anhydrideHCID 57917691HCID 57917691, compound

Product 1

HCID 57917595HCID 57917595, compoundYield 60.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of N-tert-butyl-3-(2-methyl-1-(piperazin-1-yl)propyl)benzamide (13.6 mg, 0.043 mmol), 4-amino-3-fluorobenzoic acid (10 mg, 0.065 mmol), N-ethyl-N-isopropylpropan-2-amine (11 mg, 0.086 mmol) and 1-propanephosphonic acid cyclic anhydride (55 mg, 0.086 mmol, 50% solution in ethyl acetate) in dichloromethane (2.0 mL) was stirred at room temperature for 2 hours. The mixture was treated with strong cation exchange column chromatography and purified with silica column chromatography (eluting with 33% ethyl acetate in heptane then 66% ethyl acetate in heptane) to afford the title compound (11.8 mg).

Workup

  1. additionThe mixture was treated with strong cation exchange column chromatography
  2. custompurified with silica column chromatography (
  3. washeluting with 33% ethyl acetate in heptane

Sources & evidence

ORD record
ord-5b3b190f3e764bcda93f12b20c6bd886
Source dataset
uspto-grants-2012_11
Patent number
US08314091B2

Reaction notes

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