Triethylamine → HCID 57917587, compound

HRID 1878348Notes

Reaction equation

HRID 1878348 reaction equation
CCCP1(OP(CCC)(=O)OP(CCC)(=O)O1)=O.[NH2:19][C:20]1[C:28]([F:29])=[CH:27][C:23]([C:24]([OH:26])=O)=[C:22]([F:30])[CH:21]=1.[C:31]([NH:35][C:36](=[O:50])[C:37]1[CH:42]=[CH:41][CH:40]=[C:39]([CH2:43][N:44]2[CH2:49][CH2:48][NH:47][CH2:46][CH2:45]2)[CH:38]=1)([CH3:34])([CH3:33])[CH3:32].C(N(CC)CC)C>ClCCl>[NH2:19][C:20]1[C:28]([F:29])=[CH:27][C:23]([C:24]([N:47]2[CH2:46][CH2:45][N:44]([CH2:43][C:39]3[CH:38]=[C:37]([CH:42]=[CH:41][CH:40]=3)[C:36]([NH:35][C:31]([CH3:33])([CH3:34])[CH3:32])=[O:50])[CH2:49][CH2:48]2)=[O:26])=[C:22]([F:30])[CH:21]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 111923Propylphosphonic anhydrideHCID 201514774-Amino-2,5-difluorobenzoic acidHCID 66877987N-tert-butyl-3-(piperazin-1-ylmethyl)benzamide

Product 1

HCID 57917587HCID 57917587, compoundYield 76.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-Propanephosphonic acid cyclic anhydride (2.91 g, 9.2 mmol, 2.73 mL) was added dropwise to a solution of 4-amino-2,5-difluorobenzoic acid (792.9 mg, 4.6 mmol), N-tert-butyl-3-(piperazin-1-ylmethyl)benzamide (1.3878 g, 5 mmol) and triethylamine (1.39 g, 13.9 mmol, 1.91 mL) in dichloromethane. The reaction mixture was stirred at room temperature for 1 hour. The reaction was concentrated under reduced pressure and the residue was taken up with ethyl acetate, washed with water, sodium hydrogen carbonate and brine. The organic phase was concentrated under vacuum to afford the title compound (1.52 g). MS (ESI) m/z 431.9 [M+H]+

Workup

  1. concentrationThe reaction was concentrated under reduced pressure
  2. washwashed with water, sodium hydrogen carbonate and brine
  3. concentrationThe organic phase was concentrated under vacuum

Sources & evidence

ORD record
ord-e3b6d56a9b634a87ab0e28badff3be04
Source dataset
uspto-grants-2012_11
Patent number
US08314091B2

Reaction notes

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