Triethylamine → HCID 66879318, compound

HRID 1878430Notes

Reaction equation

HRID 1878430 reaction equation
[C@H:1]([NH:5][C:6](=[O:20])[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH2:13][N:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)[CH:8]=1)([CH2:3][CH3:4])[CH3:2].[NH2:21][C:22]1[CH:30]=[CH:29][C:25]([C:26](O)=[O:27])=[CH:24][C:23]=1[F:31].C(N(CC)CC)C.CCCP1(OP(CCC)(=O)OP(CCC)(=O)O1)=O>ClCCl.C(OCC)(=O)C.C(=O)([O-])[O-].[K+].[K+]>[NH2:21][C:22]1[CH:30]=[CH:29][C:25]([C:26]([N:17]2[CH2:16][CH2:15][N:14]([CH2:13][C:9]3[CH:8]=[C:7]([CH:12]=[CH:11][CH:10]=3)[C:6]([NH:5][C@@H:1]([CH2:3][CH3:4])[CH3:2])=[O:20])[CH2:19][CH2:18]2)=[O:27])=[CH:24][C:23]=1[F:31]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 99714-Amino-3-fluorobenzoic acidHCID 111923Propylphosphonic anhydrideHCID 66878607HCID 66878607, compound

Product 1

HCID 66879318HCID 66879318, compoundYield 57.3%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolventHCID 11430Potassium CarbonateSolvent

Procedure

To a solution of (R)—N-sec-butyl-3-(piperazin-1-ylmethyl)benzamide (5.08 mmol, 1.4 g), 4-amino-3-fluorobenzoic acid (5.08 mmol, 0.789 g) and triethylamine (15.25 mmol, 2.126 mL, 1.543 g) in dichloromethane (80 mL) was added 1-propanephosphonic acid cyclic anhydride (7.63 mmol, 2.270 mL, 2.426 g, 50% solution in ethyl acetate). The reaction mixture was stirred for 1 hour then was diluted with ethyl acetate and potassium carbonate (aqueous). The organic layer was separated, dried (magnesium sulfate) and concentrated under reduced pressure. Chromatography on silica (eluting with ethyl acetate to ethyl acetate/methanol (5%)) gave the intermediate (R)-3-((4-(4-amino-3-fluorobenzoyl)piperazin-1-yl)methyl)-N-sec-butylbenzamide (1.2 g).

Workup

  1. customThe organic layer was separated
  2. dry with materialdried (magnesium sulfate)
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5ef9f36cc5d6447e91d1d95b1f8d79b2
Source dataset
uspto-grants-2012_11
Patent number
US08314091B2

Reaction notes

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